Synthetic Communications®, 35: 913-922, 2005 (^"^ Taylor & Francis

Copyright © Taylor & Francis, Inc. ^

ISSN 0039-7911 print/1532-2432 online
DOI: 10.I081/SCC-200051681

Fe-HCl: An Efficient Reagent for

Deprotection of Oximes as well as Selective
Oxidative Hydrolysis of Nitroalkenes and
Nitroalkanes to Ketones

Prasun K. Pradhan, Sumit Dey, Parasuraman Jaisankar, and

Venkatachalam S. Giri
Department of Medicinal Chemistry, Indian Institute of Chemical
Biology, Calcutta, India

Abstract: Fe-HCl mixture was found to selectively perform oxidative hydrolysis of the
nitroalkenes l a - j and nitroalkanes 2a-j to the ketones 3a-j. Also, the reagent was
observed to deprotect the oximes 7a-j to carbonyl compounds 8a-j in excellent yields.

Keywords: Deprotection of oximes, Fe, HCI, hydrolysis, ketones, nitroalkanes,

nitroalkenes, oxidation

INTRODUCTION

Nitro compounds are important intermediates in synthetic organic chemistry

because they can be converted easily into other desired functional groups. The
formation of ketones and aldebydes by oxidative hydrolysis from the correspond-
ing nitroalkanes is one of the important transformations that has tremendous
synthetic utility. Nef reaction^" involves oxidative hydrolysis of the nitronate
salts of primary or secondary nitroalkanes to aldehydes or ketones under
strong acidic conditions. Komblum et al. have used potassium permanganate

Received Novemher 11, 2004

Address correspondence to Venkatachalam S. Giri, Department of Medicinal
Chemistry, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road,
Calcutta 700 032, India. Tel.: -f 91-33-24733491; Fax: +91-33-24735197; E-mail:
vsgiri@iicb.res.in
914 P. K. Pradhan et al.

for converting nitroparaffin salts to ketones and aldehydes in good yield.'^^ It is

also known that ozonolysis of the nitroalkenes results in the formation of the
carbonyl compounds. Later it was observed by McMurry et al. that nitroalkanes
upon treatment with Ti(in)chloride followed by hydrolysis, afford the aldehydes
in good yield. In a recent review,'^"'' Ballini et al. have given an up-to-date
account of Nef reaction and its applications.

RESULTS AND DISCUSSION

In the course of preparation of some aryl ethylamine derivatives, we observed

that Fe-HCI could bdng about the oxidative hydrolysis of both secondary
nitroalkenes l a - j and nitroalkanes 2a-j to the ketones 3a-j in very good
yield (Scheme 1). Usually a mixture of iron and aqueous hydrochloric acid is
used for reduction of nitro groups to amino groups. This is the first report of
such an oxidative hydrolysis of both nitroalkanes and nitroalkenes to the
ketones using Fe and hydrochloric acid. The results are summarized in Table 1.
Interestingly, the reagent selectively converts the nitroalkenes l a - j and
nitroalkanes 2a-j that have a methyl group a- to the NO2 functionality to
the ketones 3 a - j , whereas those having an a-hydrogen 4 a - d and 5a-d are
reduced to the corresponding amines 6a-d (Scheme 2), and the yields are
summarized in Table 2.
The nitroalkenes l a - j or 4 a - d obtained from the condensation by
standard procedures of the aldehydes and nitroethane or nitromethane,
respectively, are reduced to the corresponding nitroalkanes 2 a - j or 5a-d
by using NaBH4-Dioxane-ethanol.'^'
Oximes are important derivatives used for both purification and isolation
of carbonyl compounds. Carbonyl compounds are easily converted into
oximes by refluxing with hydroxylamine hydrochloride in ethanol. The
oximes are potential intermediates in organic synthesis.^'^^ Oximes not only
serve as protecting groups for carbonyl compounds''*''^ but also have other
uses such as preparation of nitriles, preparation of amides via Beckmann
rearrangement, or to activate the carbonyl groups. However, the methods so
far developed to regenerate carbonyl compounds from oximes consist of
oxidative or reductive reaction. Most of the methods involve reagents that
are often hazardous or very toxic, expensive, or not readily available.
Although deprotection of oximes is well known, our method is a very

Fe-HCI
NO2 MeOH-HaO 0 MeOH-H2O
YNO2
3 2
Scheme 1.
An Efficient Reagent for Deprotection and Selective Oxidative Hydrolysis 915

Table 1. Conversion of nitroalkenes l a - j and nitroalkanes 2a-j to ketones 3a-j

Percent of yield
(isolated)

Entry Substrates 1 or 2 R = Products 3 From 1 From 2

a phenyl 1 -phenyl-propan-2-one 82 85
b 4-methoxyphenyl 1 -(4-methoxy-phenyl)- 80 82
propan-2-one
c 4-hydroxy-3- 1 -(4-hydroxy-3-meth- 90 95
methoxyphenyl oxy-phenyl) propan-
2-one
d 3,4,5 - trimethoxy phenyl 1 -(3,4,5-triniethoxy-phe- 80 85
nyl)propan-2-one
e 4-hydroxyphenyl 1 -(4-hydroxy-phenyl)- 81 84
propan-2-one
f 3-inciolyl l-(lH-indol-3-yl)pro- 78 85
pan-2-one
g 1 -benzo-( 1,3)dioxole-5-yl 1 -benzo-( 1,3)-dioxole-5- 85 89
yl propan-2-one
h 4-nitrophenyl 1 -(4-aniino-phenyl)pro- 83 80
pan-2-one
i 2- furyl 1 -(furan-2-yl) propan-2- 75 81
one
j 3-nitro-4-(methoxycar- 6-(2-oxo-propyl)-4H- 92 95
bonylmethoxy)- benzo-( 1,4)-oxazin-3-
phenyl one

simple, efficient, and facile method for deprotection of oximes (Scheme 3).
The yields of carbonyl compounds 8 a - j from their oximes 7 a - j are
summarized in Table 3. The reaction takes place only when a mixture of Fe
and HCl is used but does not occur in the absence of one of them (Fe or HCl).
It is well known that reduction of nitro groups to the amines takes place
through the intermediacy of the nitroso derivatives of the oximes. We believe
that in the cases of nitroalkenes l a - j and nitroalkanes 2a-j, because of
the presence of a methyl group a to the NO2 functionality, oximes
are generated that subsequently undergo oxidative hydrolysis to the ketones
3 a - j . On the other hand, nitroalkenes 4a-d and nitroalkanes 5a-d are

R Fe-HCl R ^Fe-HCl F

NH2 MeOH-HjO NO2

6 5

Scheme 2.
916 P. K. Pradhan et al.

Table 2. Conversion of nitroalkenes 4a-d and nitroalkanes 5a-d to the amines 6a-d

Percent yield of 6 (isolated)

Entry Substrate 4 or 5 From 4 From 5

a 3,4,5- trimethoxyphenyl 72 75
b benzo-( 1,3)-ciioxole-5-yl 70 71
c phenyl 63 65
d 3-indolyl 71 76

converted to the nitroso group, which spontaneously undergoes reduction to the

corresponding amines 6a-d through the intermediacy of the hydroxylamines.
In conclusion, the Fe and aq. HCl system is an efficient reagent for
deprotection of oximes and also for selective conversion of both nitroalkenes
and nitroalkanes to the same ketones.

EXPERIMENTAL

All melting points were determined in open capillaries on SPAC-N-SERVICE

(India) capillary melting point apparatus and are uncorrected. IR spectra were
recorded on a JASCO-FT-IR Model 410 using samples as KBr plates.
' H N M R (300 MHZ) and '^C NMR (75 MHz) were recorded on a Bruker
DPX 300 NMR instrument using TMS as internal standard. Elemental
analyses were done on a PERKIN ELMER 2400 Series II CHNS/0
analyzer. Mass spectra ESI and EI were recorded on Q-TOF Micro mass
(LCMS) spectrometer and JEOL-AX-500 spectrometer respectively.

Typical Experimental Procedure for Conversion of Nitro Alkanes

or Nitro Alkenes or Oximes to Carbonyl Compounds

To a solution of nitroalkane or nitroalkene or oxime (3 mmol) in a mixture

of MeOH (5mL), HjO (2mL), and cone. HCl (2mL), iron dust (336 mg;
6 mmol) was added in portions and the resulting reaction mixture was

Fe-HCl R
>-
MeOH-HzO ^2
• > -
8
Scheme 3.
An Efficient Reagent for Deprotection and Selective Oxidative Hydrolysis 917

Tabte 3. Conversion of oximes 7a-j to the corresponding carbonyl compounds 8a-j

Percent
Entry Oximes 7 Carbonyl compounds 8 yield of 8

a Benzaldehyde oxime Benzaldehyde 94

b Benzo( 1,3)dioxole-5-carbal- Benzo( 1,3)dioxole-5- 85
dehyde oxime carbaldehyde
c Chroman-4-one-oxime Chroman-4-one 80
d 6-(2-Hydroxyamino-pro- 6-(2-Oxo-propyl)-4H-ben- 82
pyl)-4H-benzo(l ,4)oxa- zo( 1,4)oxazine-3-one
zine-3-one
e Furan-2-carbaldehyde oxime Furan-2-aldehyde 81
f 4-Nitro-benzaldehyde oxime 4-amino-benzaldehyde 90
g 1 -(4-Hydroxy-3-methoxy- 1 -(4-Hydroxy-3-methoxy- 82
phenyl)-propan-2-one phenyl)-propan-2-one
oxime
h 1-Phenyl-ethanone oxime 1 -Phenyl-ethanone 84
i Diphenyl-methanone oxime Diphenyl-methanone 81
j 4-Methoxy benzaldehyde 4-Methoxy benzaldehyde 90
oxime

refluxed over a steam bath for 30 min. After complete disappearance of

the starting material (monitored by TLC using 1% MeOH in CHCI3), the
reaction mixture was filtered over a bed of celite using MeOH. The
filtrate was concentrated and diluted with H2O (10 mL) either basified in
the case of amitie products or directly extracted with CHCI3 (3 x 10 mL).
The CHCI3 layer was then dried (Na2SO4), the solvent was removed under
reduced pressure, and the residue was chromatographed over silica gel
using increasing concentrations of CHCI3 in petroleum ether or direct crystal-
lization to the desired ketone in pure form. The compounds have been charac-
terized mainly from their physical data, particularly NMR, and confirmed by
comparison with authentic specimens obtained by standard procedures.
The following compounds are already known in the literature: la,'^^ lb,'^^
'^l t«' t^] f51 ['O] ['" l'^l f^

[251 [26] [28]

l,2,3-Trimethoxy-5-(2-nitro-propenyl)benzene (Id). Mp 66-68°C;

IR (KBr): u = 2940, 2223, 1582, 943, 851cm"'; ' H NMR (CDCI3):
5 = 2.49 (s, 3H), 3.90 (s, 9H), 6.66 (s, 2H), 6.86 (s, IH); MS (ESI): 254
(M-|-H)+. Anal, calcd. for C^HisNOs: C, 56.91; H, 5.97; N, 5.53. Found:
C, 56.79; H, 6.01; N, 5.60.
3-(2-Nitro-propenyl)-lH-indole (If), Mp 186-188 °C; IR (KBr):
v = 3425, 1627, 1525, 1478, 1269, 1222, 1126, 971, 857, 750cm"'; ' H
NMR (CDCI3): S = 2.54 (s, 3H), 7.27-7.36 (m, 2H), 7.46 (d, 7 = 6.8 Hz,
918 P. K. Pradhan et al.

IH), 7.57 (s, IH), 7.83 (d, 7 = 7.2Hz, IH), 8.52 (s, IH), 8.74 (brs, NH); MS
(ESI): 203 (M + H)+. Anal, calcd. for C11H10N2O2: C, 65.34; H, 4.98; N,
13.85. Found; C, 65.50; H, 5.02; N, 13.91.
[2-Nitro-4-(2-nitro-propenyl)-phenoxy]aceticacid methyl ester
(lj). Liquid; IR (neat); v = 3429, 1641 cm"'; ' H NMR (CDCI3); 8 = 2.46
(s, 3H), 3.83 (s, 3H), 4.86 (s, 2H), 7.06 (d, 7 = 8 . 7 Hz, IH), 7.59
(d, 7 = 8 . 7 H z , IH), 7.98 (s, IH), 8.0 (d, 7 = 5 . 1 Hz, IH); MS (ESI);
297(M + H)+. Anal, calcd. for C12H12N2O7; C, 54.90; H, 4.6t; N, 9.15.
Eound; C, 55.01; H, 4.67; N, 9.21.
l-Methoxy-4-(2-nitro-propyl)benzene (2b). Liquid; IR (neat);
u = 2937, 1610, 1549, 757 cm"'; 'HNMR (CDCI3): S = 1 . 5 2
(d, 7 =6.9Hz, 3H), 2.95 (dd, 7 =6.66Hz, 14.0Hz, IH), 3.24 (dd,
7 = 6.65Hz, 14.0Hz, IH), 3.77 (s, 3H), 4.72 (sext, 7 = 6.76Hz, IH), 6.83
(d, 7 = 8.56 Hz, 2H), 7.07 (d, 7 = 8.22 Hz, 2H); MS (ESI): 196 (M + H)+.
Anal, calcd. for C10H13NO3: C, 61.53; H, 6.71; N, 7.18. Found; C, 61.42;
H, 6.78; N, 7.27.
2-Methoxy-4-(2-nitro-propyl)phenot (2c). Liquid; IR (neat):
i, = 3471, 1548, 1032, 797cm"'; ' H NMR (CDCI3): 5 = 1 . 5 3
(d, 7 =6.64Hz, 3H), 2.94 (dd, 7=6.66Hz, 14.01 Hz, IH), 3.24 (dd,
7 = 7.50Hz, 14.01 Hz, IH), 3.86 (s, 3H), 4.73 (sext, 7 = 6.70Hz, IH), 5.61
(brs, OH), 6.56 (s, IH), 6.65 (d, 7 = 9.9Hz, IH), 6.95 (d, 7 = 8.2Hz, IH);
MS (ESI): 212 (M + H)+. Anal, calcd. for C,oH|3N04: C, 56.86; H, 6.20;
N, 6.63. Found; C, 56.68; H, 6.28; N, 6.71.
l,2,3-Trimethoxy-5-(2-nitro-propyl)benzene (2d). Liquid; IR (neat):
11 = 3430, 1549, 922cm"'; ' H NMR (CDCI3): 5 = 1 . 5 6 (d, 7 = 6 . 6 H z ,
3H), 2.94 (dd, 7 = 6.6Hz, 14.0Hz, IH), 3.28 (dd, 7 = 6.6Hz, 14.0Hz, IH),
3.82 (s, 9H), 4.73 (sext, 7 =6.64Hz, IH), 6.36 (s, 2H); MS (ESI): 256
(M + H)+. Anal, calcd. for C^HnNOs: C, 56.46; H, 6.71; N, 5.49. Found:
C, 56.34; H, 6.80; N, 5.57.
4-(2-Nitropropyt)pbenot (2e). Liquid; IR (neat): v = 3390, 1546,
770cm"'; ' H NMR (CDCI3): 8 1.53 (d, 7 = 6 . 9 H z , 3H), 2.94 (dd,
7 =6.5Hz, 14.0Hz, IH), 3. 23 (dd, 7 =6.6Hz, 14.0Hz, IH), 4.73 (sext,
7 = 6 . 5 Hz, IH), 5.29 (brs, OH), 6.78 (d, 7 = 6 . 9 Hz, 2H), 7.04
(d, 7 = 6.9Hz, 2H); MS (ESI): 182 (M + H)+. Anal, calcd. for C9H,iNO3:
C, 59.66; H, 6.12; N, 7.73. Found: C, 59.54; H, 6.89; N, 7.81.
3-(2-Nitro-propyt)-lH-indole (2f). Liquid; IR (neat): v = 3417, 1546,
745 cm"'; ' H NMR (CDCI3): 8= 1.523 (d, 7 = 6 . 2 H z , 3H), 3.16 (dd,
7 = 6 . 2 H z , 14.5HZ, IH), 3.44 (dd 7 = 7 . 2 H z , 14.5 Hz, IH), 4.85 (sext,
7 = 6.3Hz, IH), 6.91 (s, IH), 7.08-7.17 (m, 2H), 7.30 (d, 7 = 7.6Hz, IH),
7.54 (d, 7 = 7.6Hz, IH), 8.03 (brs, NH); MS (ESI); 205 (M + H)+. Anal,
calcd. for C,,H,2N2O2: C, 64.69; H, 5.92; N, 13.72. Found: C, 64.54; H,
5.99; N, 13.83.
5-(2-Nitro-propyl)benzo(l,3)dioxole (2g). Liquid; IR (neat):
u = 2900, 1550, 930cm"'; ' H NMR (CDCI3): 5 = 1 . 5 3 (d, 7 = 6 . 6 H z ,
An Efficient Reagent for Deprotection and Selective Oxidative Hydrolysis 919

3H), 2.92 (dd, y = 6.6HZ, 14.0 Hz, lH), 3.22 (dd, 7 = 7.6 Hz, 14.0 Hz, lH),
4.71 (sext, y = 6.8Hz, lH), 5.93 (s, 2H), 6.61 (d, 7 = 7.8Hz, lH), 6.63
(s, lH), 6.74 (d, J = 7.8Hz, lH); MS (ESI): 210 (M + H)+. Anal, calcd. for
C|oHnN04: C, 57.41; H, 5.30; N, 6.70. Found: C, 57.30; H, 5.39; N, 6.78.
2-(2-Nitro-propyl)furan (2i). Liquid; IR (neat): u = 3420, 1537,
756cm"'; ' H NMR (CDCI3): S = 1 . 5 7 (d, y = 6.7Hz, 3H), 2.37 (dd,
y = 7 . 2 H z , 15.2HZ, lH), 3.80 (dd, y = 6 . 7 H z , 15.2Hz, lH), 4.84 (sext,
7 = 6 . 8 Hz, lH), 6.13 (d, 7 =2.53 Hz, lH), 6.30 (d, 7 = 2 . 8 Hz, lH), 7.33
(s, lH); MS (ESI): 156 (M + H)+. Anal, calcd. for C7H9NO3; C, 54.19; H,
5.85; N, 9.03. Found: C, 54.05; H, 5.92; N, 9.10.
(2-Nitro-4-(2-nitro-propyl)phenoxy(acetic acid methyl ester
(2j). Liquid; IR (neat): u = 3439, 1743, 1626, 814, 755cm~'; ' H NMR
(CDCI3): 5 = 1.59 (d, 7 = 6.7 Hz, 3H), 3.04 (dd, 7 = 5.8 Hz, 14.4 Hz, lH),
3.30 (dd, 7 = 8.3Hz, 14.4Hz, lH), 3.80 (s, 3H), 4.74 (s, 2H), 4.75-4.80
(m, lH), 6.94 (d, 7 = 8.6Hz, lH), 7.30 (d, 7 = 8.6Hz, lH), 7.71 (s, lH);
MS (ESI): 299 (M + H)+. Anal, calcd. for C12H14N2O7: C, 48.32; H, 4.73;
N, 9.39. Found: C, 48.21; H, 4.80; N, 9.46.
l-(3,4,5-Trimethoxy-phenyl)propan-2-one (3d). Liquid; IR (neat):
11 = 3513, 1710, 1590, 917cm~'; ' H NMR (CDCI3): 5 = 2.18 (s, 3H), 3.63
(s, 2H), 3.84 (s, 9H), 6.41 (s, 2H); MS (ESI): 225 (M + H)+: Anal, calcd.
for C,2H|6O4: C, 64.27; H, 7.19. Found: C, 64.41; H, 7.26.
l-(4-Hydroxy-phenyl)propan-2-one (3e). Liquid; IR (neat):
u = 3357, 1698, 1513, 757cm"'; ' H NMR (CDCI3): 6 = 2.16 (s, 3H), 3.63
(s, 2H), 6.40 (brs, OH), 6.80 (d, 7 =8.30 Hz, 2H), 7.02 (d, 7 =8.30 Hz,
2H); MS (ESI): 151 (M + H)+. Anal, calcd. for C9H10O2: C, 71.98; H,
6.7L Found: C, 71.86; H, 6.77.
l-(lH-Indol-3-yl)propan-2-one (3f). Mp 104-106°C. IR (KBr):
u = 3327, 1708, 752cm~'; ' H NMR (CDCI3): S = 2.15 (s, 3H), 3.8
(s, 2H), 7.07 (s, lH), 7.10-7.23 (m, 2H), 7.34 (d, 7 = 7.71 Hz, lH), 7.52
(d, 7 = 7.71 Hz, lH), 8.2 (brs, NH); MS (ESI): 174 (M + H)+. Anal, calcd.
forCiiHiiNO: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.13; H, 6.46; N, 8.15.
l-(4-Amino-phenyl)propan-2-one (3h). Liquid; IR (neat): v = 3363,
1703, 1624, 1515cm"'; ' H NMR (CDCI3): 5 = 2.14 (s, 3H), 3.57 (s, 2H),
4.17 (brs, NH2), 6.49 (d, 7 = 8.41 Hz, 2H), 7.14 (d, 7 = 7.95 Hz, 2H); MS
(ESI): 150 (M + H)+. Anal, calcd. for CgHnNO: C, 72.46; H, 7.43; N,
9.39. Found: C, 72.33; H, 7.50; N, 9.48.
l-Furan-2-yl-propan-2-one(3i). Liquid; IR (neat): v = 3282, 2923,
1712, 743 cm"'; ' H NMR (CDCI3): S = 1.88 (s, 3H), 3.52 (s, 2H), 6.12
(d, 7 =2.22 Hz, lH), 6.20 (d, 7 =2.90 Hz, lH), 7.33 (s, lH); MS (ESI):
125 (M + H)+. Anal, calcd. for C7H8O2: C, 67.73; H, 6.50. Found: C,
67.99; H, 6.58.
6-(2-Oxo-propyl)-4H-benzo(l,4(oxazine-3-one (3j). Mp 154-156°C;
IR (KBr): i; = 3197, 1710, 1688, 800cm"'; ' H NMR (CDCI3): 5 = 2.18
(s, 3H), 3.64 (s, 2H), 4.61 (s, 2H), 6.67 (s, lH), 6.79 (d, 7 = 8.16Hz, lH),
920 P. K. Pradhan et al.

6.93 (d, 7 = 8.16Hz, IH), 8.86 (hrs, NH); '^C NMR (CDCI3): (S = 29.82,
50.25, 67.51, 117.28, 117.50, 125.56, 126.75, 129.08, 143.12, 166.80, and
206.79; MS (ESI): 206 (M-fH)+. Anal, calcd. forC,|HnNO3: C, 64.38; H,
5.40; N, 6.83. Found: C, 64.50; H, 5.59; N, 6.90.
2-(3,4,5-Trimethoxy-phenyl)ethylamine (6a). Liquid; IR (neat):
V = 3412, 1645, 996, 826cm"'; ' H NMR (CDCI3): 5 = 2.73 (t, 7 = 6.78Hz,
2H), 2.98 (t, J = 6.74 Hz, 2H), 2.91 (brs, 2 x NH), 3.84 (s, 9 H), 6.43 (s, 2H);
'^C NMR (CDCI3): (5 = 39.02, 46.12, 61.27 (2 x C), 65.78, 111.01 (2 x C),
137.95, 141.82, 158.42 (2 x C); MS: 212 (M-l-H)+. Anal, calcd. for
Ci,H|7NO3: C, 62.54; H, 8.11; N, 6.63. Found: C, 62.42; H, 8.15: N, 6.69.
2-Benzo(l,3(dioxole-5-yl-etbylaniine (6b). Liquid; IR (neat):
u = 3412, 1653, 809cm"'; ' H NMR (CDCI3): 8 1.74 (hrs, NH2), 2.66
(t, 7 =6.69 Hz, 2H), 2.91 (t, 7 =6.57 Hz, 2H), 5.91 (s, 2H), 6.50-6.80
(m, 3H); MS (ESI): 166 (M + H)+. Anal, calcd. for C9HnNO2: C, 65.44;
H, 6.71; N, 8.48. Found: C, 65.31; H, 6.78, N, 8.54.
6-(2-Hydroxyimino-propyl)-4H-benzo-(l,4)oxazine-3-one (7d). Mp
143-144°C; IR (KBr): i; = 3216, 1688, 806cm~'; ' H NMR (CDCI3):
5 = 1.65 (s, 3H), 3.16 (s, 2H), 3.18 (s, 2H), 6.70-7.06 (m, 3, H), 10.49
(hrs, IH), 10.66 (s, IH); '^C NMR (DMSO-dg): (S = 13.78, 41.48, 67.59,
116.76, 116.89, 124.25, 128.11, 132.57, 142.77, 155.28, 165.83; MS (ESI):
221 (M-|-H)+. Anal, calcd. for C11H12N2O3: C, 59.99; H, 5.49; N, 12.72.
Found: C, 59.83; H, 5.54; N, 12.78.
l-(4-Hydroxy-3-metboxy-pbenyl)propan-2-one oxime (7g). Liquid;
IR (neat): u = 3370, 1661, 1514, 793cm"'; ' H NMR (CDCI3): 5 = 1.79
(s, 3H), 3.41 (s, 2H), 3.79 (s, 3H), 3.85 (s, lH), 6.66-6.90 (m, 4H); MS
(ESI): 196 (M + H)+. Anal, calcd. for C,oH|3N03: C, 61.53; H, 6.71; N,
7.18. Found: C, 61.42; H, 6.79; N, 7.24.

ACKNOWLEDGMENT

S. D. thanks University Grants Commission, New Delhi, India, for Junior

Research Fellowship and the other authors thank Council of Scientific and
Industrial Research, New Delhi, India, for the generous grant.

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