Convenient preparation of O-alkylhydroxamic acids using 2-acylpyridazin-3(2H)-ones

Article abstract of DOI:10.1081/SCC-200050375

Treatment of O-alkylhydroxylamine hydrochlorides with 2-acyl-4,5- dichloropyridazin-3(2H)-ones in the presence of triethylamine or Amberlite IRA-67 in acetonitrile gave corresponding O-alkylhydroxamic acid derivatives in excellent yields. This is an effic

Full text of DOI:10.1081/SCC-200050375

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Convenient Preparation of O‐Alkylhydroxamic
Acids Using 2‐Acylpyridazin‐3(2H)‐ones
Jeum‐Jong Kim a , Young‐Dae Park a , Ho‐Kyun Kim a , Su‐Dong Cho a ,
Ju‐Kyeong Kim a , Sang‐Gyeong Lee b & Yong‐Jin Yoon a
a Department of Chemistry and Environmental Biotechnology, National Core
Research Center, Gyeongsang National University, Chinju, Korea
b Department of Chemistry and Research Institute of Life Science,
Gyeongsang National University, Chinju, Korea
Published online: 20 Aug 2006.
To cite this article: Jeum‐Jong Kim , Young‐Dae Park , Ho‐Kyun Kim , Su‐Dong Cho , Ju‐Kyeong Kim ,
Sang‐Gyeong Lee & Yong‐Jin Yoon (2005) Convenient Preparation of O‐Alkylhydroxamic Acids Using
2‐Acylpyridazin‐3(2H)‐ones, Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 35:5, 731-738, DOI: 10.1081/SCC-200050375
To link to this article: http://dx.doi.org/10.1081/SCC-200050375
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Synthetic Communicationsw, 35: 731–738, 2005
Copyright # Taylor & Francis, Inc.
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1081/SCC-200050375
Convenient Preparation of
O-Alkylhydroxamic Acids Using
2-Acylpyridazin-3(2H)-ones
Jeum-Jong Kim, Young-Dae Park, Ho-Kyun Kim,
Su-Dong Cho, and Ju-Kyeong Kim
Department of Chemistry and Environmental Biotechnology, National
Core Research Center, Gyeongsang National University, Chinju, Korea
Sang-Gyeong Lee
Department of Chemistry and Research Institute of Life Science,
Gyeongsang National University, Chinju, Korea
Yong-Jin Yoon
Department of Chemistry and Environmental Biotechnology, National
Core Research Center, Gyeongsang National University, Chinju, Korea
Abstract: Treatment of O-alkylhydroxylamine hydrochlorides with 2-acyl-4,5-
dichloropyridazin-3(2H)-ones in the presence of triethylamine or Amberlitew
IRA-67 in acetonitrile gave corresponding O-alkylhydroxamic acid derivatives in
excellent yields. This is an efficient, convenient, and eco-friendly method.
Keywords: Hydoxamic acid, O-alkylhydroxamic acid, 2-acyl-4,5-dichloropyridazin-
3(2H)-ones, Amberlitew IRA-67
Received in Japan 24 May 2004
Address correspondence to Yong-Jin Yoon, Department of Chemistry and
Environmental Biotechnology, National Core Research Center, Gyeongsang
National University, Chinju 660-701, Korea. Fax: 082-055-761-0244; E-mail:
yjyoon@nongae.gsnu.ac.kr

732
J.-J. Kim et al.
Hydroxamic acids which are well known to bind with hard metal ions,[1–3] are
important in many chemotherapeutic agents such as the succinate-based
matrix metalloproteinases (MMPs) inhibitors,[1] the class I/II histone deace-
tylase (HDAC) inhibitors,[2] and iron-containing antibiotics.[4] Preparative
methods and their applications have been studied for over a century.[5]
Recently, various methods were reported for the preparation of hydroxamic
acids starting from carboxylic acids or their derivatives,[3,6] and N-acyloxazo-
lidinones.[7] Although some of these methods are quite efficient for the prep-
aration of substituted hydroxamic acids, these methods have some drawbacks
that limit their application: instability, toxicity, high volatility of acylating
agents such as acid chlorides or activated esters, the formation of by-product,
high cost and/or difficult purification, and also their dependence on the
amine. Therefore, development of novel convenient methods is important for
efficient synthesis of hydroxamic acids from carboxylic acid derivatives.
This paper reports on a novel and convenient method for the synthesis of
hydroxamic acid derivatives using 2-acyl-4,5-dichloropyridazin-3(2H)-ones.
In our previous reports,[8,9] we demonstrated that 2-acyl-4,5-dichloropyridazin-
3(2H)-ones are excellent acylating agents for the amines. Pyridazin-3(2H)-
ones are useful N-heterocycles as a good leaving group or activator in
synthetic chemistry.[8–10] Thus, the postmodification of this functionality to
others is of interest to those involved in synthetic chemistry.
RESULTS AND DISCUSSION
Our initial goal was to evaluate the conversion potentiality of 2-acylpyridazin-
3(2H)-ones to hydroxamic acids. From the preliminary experiments, we
selected the triethylamine/acetonitrile system as a suitable base and solvent.
Reaction of some O-alkyl-hydroxylamine hydrochlorides 1 with 2-acylpyrida-
zin-3(2H)-ones 2 in the presence of triethylamine in acetonitrile at room
temperature gave the corresponding O-alkylhydroxamides 3 in good to
excellent yields (Method A in Table 1). On the other hand, compounds O-
alkylhydroxylamine hydrochlorides 1a-d reacted with 2 in the presence of
Amberlitew IRA-67 resin in acetonitrile instead of triethylamine at room
temperature to afford 3a-l in excellent yields (Method B in Table 1).
Treatment of O-trimethylsilylhydroxylamine (1d) with 2a in the presence of
triethylamine or Amberlitew IRA-67 gave free hydroxamic acid 3i in
excellent yields (Entry 11). However, we could not obtain only N-hydroxy-
benzamide (3i) by the reaction of hydroxylamine hydrochloride with 2a
under the same conditions (Scheme 1).
We also obtained O-benzyloxybenzamide (3a) in excellent yield by the
reaction of O-benzylhydroxylamine hydrochloride with 2a using recovered
Amberlitew IRA-67 under the same condition (reused two times for Entry 2

Preparation of O-Alkylhydroxamic Acids
733
Table 1. Preparation of O-substituted-hydroxamide 3 using 2 in the presence of a
base in acetonitrile
Method A
Method B
Time Yield Time Yield
(%)a
Entry
3
R
R1
C6H5-
C6H5-
(min)
(%)a
(min)
1
2
A
A
A
B
C
D
E
F
C6H5CH2-
C6H5CH2-
C6H5CH2-
C6H5CH2-
C6H5CH2-
C6H5CH2-
C6H5CH2-
CH255CHCH2-
CH3-
5
—
—
20
37
65
12
105
100
35
29
5
91
—
—
96
89
82
95
94
85
96
70
93
86
90
45
45
40
35
30
25
35
45
40
25
50
10
30
30
95
96b
94c
98
99
89
98
98
98
94
90
95
84
92
3
C6H5-
4
p-CH3C6H4-
p-ClC6H4-
2,4-Cl2C6H3-
p-MeOC6H4
p-MeOC6H4
p-MeOC6H4
C4H3Od-
5
6
7
8
9
G
H
ie
10
11
12
13
14
C6H5CH2-
H-
C6H5-
n-C4H9-
J
C6H5CH2-
CH255CHCH2-
C6H5CH2-
K
L
n-C4H9-
c-C6H11-
30
40
aIsolated yields.
bThe first recovered resin was used.
cThe second recovered resin was used.
d2-Furoyl.
eRONH2.HCl is [(CH3)3Si]ONH2.
and reused three times for Entry 3). Amberlitew IRA-67 resin can be
used repeatedly after washing with methanol. Therefore, from the environ-
mental and economical points of view, the use of the resin in our reaction
is superior to triethylamine for the preparation of hydroxamic acids. In
all cases, the reusable 4,5-dichloropyridazin-3(2H)-one was also recovered
quantitatively.
In conclusion, our method is an efficient, convenient, and eco-friendly
method, especially in the case of Method B. It also has some advantages:
easy preparation and the stability of compound 2, easy work-up, and the
quantitative recovery of pyridazinone and Amberlitew IRA-67 resin.

734
J.-J. Kim et al.
Scheme 1.
EXPERIMENTAL
Reagents and solvents were used as received from commercial sources. The
TLC was performed on plates coated with silica gel (silica gel 60 F254,
Merck). The spots were located by ultraviolet, (UV) light. Column chromato-
graphy was carried out on silica gel (silica gel 60, 70–230 mesh). Melting
points were determined with a Thomas-Hoover capillary apparatus and are
1
uncorrected. H and 13C NMR spectra were obtained on a Bru¨ker FT NMR-
DRX 500 or Varian Inova 500 Spectrometer. The chemical shift values are
reported in d units (part per million) relative to tetramethyl selane (TMS) as
an internal standard. Infrared (IR) spectra were obtained on a Hitachi 270-
50 or Mattson Genesis Series FT-IR spectrophotometer. Elemental analyses
were performed with a Perkin Elmer 240C.
General Procedure
Method A
A mixture of hydroxylamine hydrochlorides (0.63 mmol), 2-acyl-4,5-
dichloropyridazin-3(2H)-ones 2[8] (0.69 mmol), triethylamine (0.75 mmol),
and acetonitrile (15 mL) was stirred until compound 2 disappeared. After
filtering the reaction mixture, the solvent was evaporated under reduced
pressure, and the resulting residue was applied to the top of an open-bed
silica gel column (3 Â 10 cm), and the column was eluted with CH2Cl2:diethyl

Preparation of O-Alkylhydroxamic Acids
735
ether ¼ 10:1 (v/v). The fractions containing hydroxamides were combined
and evaporated under reduced pressure to afford the corresponding O-alkyl-
hydroxamic acids 3 in good to excellent yields. The fractions containing
4,5-dichloropyridazin-3(2H)-one were also combined and evaporated under
reduced pressure to recover it in quantitative yield.
Method B
A mixture of hydroxylamine hydrochlorides (1, 1.26 mmol), 2-acyl-4,5-
dichloropyridazin-3(2H)-ones 2[8] (1.38 mmol), Amberlitew IRA-67
(1.0 g/mmol for NH2OR.HCl) and acetonitrile (15 mL) was stirred until
compound 2 disappeared. After filtering the reaction mixture, the solvent
was evaporated under reduced pressure, and the resulting residue was
applied to the top of an open-bed silica gel column (3 Â 10 cm), and the
column was eluted with CH2Cl2:diethyl ether ¼ 10:1 (v/v). The fractions
containing hydroxamides were combined and evaporated under reduced
pressure to afford the corresponding O-alkylhydroxamic acids 3 in good to
excellent yields. The fractions containing 4,5-dichloropyridazin-3(2H)-one
were also combined and evaporated under reduced pressure to recover it in
quantitative yield. The filtrate was washed with methanol (20 mL Â 3) and
dried in an oven at 40–508C to give Amberlitew IRA-67 resin that can be
reused.
N-Benzyloxybenzamide (3a). Colorless solid; M.p. 868C; IR (KBr)
3350, 3030, 2980, 1650, 1580, 1510, 1480, 1460, 1300, 1290 cm21 1H
;
NMR(CDCl3) d 9.07 (s, NH, D2O exchangeable), 7.67–7.70 (m, Ar-2H),
7.36-7.53 (m, Ar-8H), 5.02 (s, 2H); 13C NMR(CDCl3) d 78.33, 127.12,
128.61, 128.65, 128.76, 129.32, 131.92, 132.03, 135.28, 166.49. Anal.
Calcd. for C14H13NO2: C, 73.99; H, 5.77; N, 6.16. Found: C, 73.98; H,
5.75; N, 6.69; Elution solvent for the column ¼ CH2Cl2:THF (40:1, v/v);
Rf ¼ 0.73 (CH2Cl2:THF ¼ 19:1, v/v).
N-Benzyloxy-4-methylbenzamide (3b). Colorless solid; M.p. 1288C; IR
(KBr) 3200, 3030, 2970, 1660, 1500, 1320 cm21; 1H NMR(DMSO-d6) d 11.70
(s, NH, D2O exchangeable), 7.67 (d, Ar-2H, J ¼ 9.0 Hz), 7.25–7.47
(m, Ar-7H), 4.93 (s, 2H), 2.34(s, 3H); 13C NMR(DMSO-d6) d 20.95, 76.97,
127.08, 128.24, 128.28, 128.86, 128.93, 129.49, 135.96, 141.53, 164.41.
Anal. Calcd. for C15H15NO2: C, 74.67; H, 6.27; N, 5.81. Found: C, 74.48;
H, 6.45; N, 5.60; Elution solvent for the column ¼ CH2Cl2:THF (40:1,
v/v); Rf ¼ 0.73 (CH2Cl2:THF ¼ 40:1, v/v).
N-Benzyloxy-4-chlorobenzamide (3c). Colorless solid; M.p. 1588C; IR
(KBr) 3150, 2950, 1660, 1600, 1500, 1500, 1320, 1200, 1180, 1100, 1040,
1
1030, 900, 860, 760, 740 cm21; H NMR(DMSO-d6) d 11.88 (s, NH, D2O
exchangeable), 7.79 (d, Ar-2H, J ¼ 8.4 Hz), 7.55 (d, Ar-2H, J ¼ 8.4 Hz),
7.45-6.59(m, Ar-5H), 4.95 (s, 2H); 13C NMR(DMSO-d6) d 77.06, 128.30,

736
J.-J. Kim et al.
128.31, 128.55, 128.92, 129.00, 131.05, 135.81, 136.44, 163.39. Anal. Calcd.
for C14H12NO2Cl: C, 64.25; H, 4.62; N, 5.35; Cl, 13.55. Found: C, 64.36; H,
4.65; N, 5.40; Cl, 13.59. Elution solvent for the column ¼ CH2Cl2:THF (40:1,
v/v); Rf ¼ 0.48 (CH2Cl2:diethyl ether ¼ 9:1, v/v).
N-Benzyloxy-2,4-dichlorobenzamide (3d). Colorless solid; M.p. 1428C;
1
IR (KBr) 3200, 3020, 3000, 1670, 1600, 1530, 1480, 1390, 1330 cm21; H
NMR(DMSO-d6) d 11.68 (s, NH, D2O exchangeable), 7.70 (s, Ar-1H), 7.34–
7.50 (m, Ar-7H), 4.95 (s, 2H); 13C NMR(DMSO-d6) d 77.06, 127.36, 128.30,
128.36, 128.95, 129.25, 130.61, 131.81, 132.75, 135.17, 135.64, 162.32.
Anal. Calcd. for C14H11Cl2NO2: C, 56.78; H, 3.74; Cl, 23.94; N, 4.73. Found:
C, 55.76; H, 3.63; Cl, 23.84; N, 4.65; Elution solvent for the column ¼ CH2Cl2:
THF (40:1, v/v); Rf ¼ 0.43 (CH2Cl2:diethyl ether ¼ 9:1, v/v).
N-Benzyloxy-4-methoxybenzamide (3e). Colorless solid; M.p. 1138C;
IR (KBr) 3270, 3050, 2960, 1640, 1620, 1500, 1320 cm21
;
1H
NMR(DMSO-d6) d 11.62 (s, NH, D2O exchangeable), 7.51 (d, Ar-2H,
J ¼ 9.0 Hz), 7.35–7.46 (m, Ar-5H), 6.99(d, Ar-2H, J ¼ 9.0 Hz), 4.91
(s, 2H), 3.80(s, 3H); 13C NMR(DMSO-d6) d 55.34, 76.98, 113.68, 124.40,
128.23, 128.28, 128.85, 128.91, 136.02, 161.83, 164.17. Anal. Calcd. for
C15H15NO3: C, 70.02; H, 5.88; N, 5.44. Found: C, 70.48; H, 5.95; N, 5.50;
Elution solvent for the column ¼ CH2Cl2:THF (40:1, v/v); Rf ¼ 0.48 (CH2-
Cl2:diethyl ether ¼ 9:1, v/v).
N-Allyloxy-4-methoxybenzamide (3f). Colorless solid; M.p. 508C; IR
(KBr) 3250, 3000, 1650, 1620, 1500, 1320, 1280, 1200, 1160 cm21 1H
;
NMR(DMSO-d6) d 11.56 (s, NH, D2O exchangeable), 7.76(d, Ar-2H,
J ¼ 8.4 Hz), 7.01 (d, Ar-2H, J ¼ 9.0 Hz), 5.97–6.06(m, 1H), 5.25–
5.38(m, 2H), 4.43(d, 2H, J ¼ 5.7 Hz), 3.81(s, 3H); 13C NMR(DMSO-d6)
d 55.32, 76.05, 113.68, 119.03, 124.44, 128.92, 133.27, 161.86, 164.12.
Anal. Calcd. for C11H13NO3: C, 63.76; H, 6.32; N, 6.76. Found: C, 63.28;
H, 6.45; N, 6.69; Elution solvent for the column ¼ ethyl acetate:n-hexane
(1:2, v/v); Rf ¼ 0.19 (CH2Cl2:diethyl ether ¼ 7:1, v/v).
N,4-Dimethoxybenzamide (3g). Colorless solid; M.p. 948C; IR (KBr)
3170, 2950, 1660, 1620, 1500, 1300, 1260 cm21 1H NMR(DMSO-d6)
;
d 11.59 (s, NH, D2O exchangeable), 7.74(d, Ar-2H, J ¼ 9.0 Hz), 7.00
(d, Ar-2H, J ¼ 9.0 Hz), 3.81(s, 3H), 3.70(s, 3H); 13C NMR(DMSO-d6)
d 55.33, 63.21, 113.68, 124.36, 128.85, 161.83, 163.87. Anal. Calcd. for
C9H11NO3: C, 59.66; H, 6.12; N, 7.73. Found: C, 59.75; H, 6.27; N, 7.80;
Elution solvent for the column ¼ CH2Cl2:THF (40:1, v/v); Rf ¼ 0.27 (CH2-
Cl2:diethyl ether ¼ 7:1, v/v).
N-Benzyloxy-2-furamide (3h). Colorless solid; M.p. 998C; IR (KBr) 3200,
1
3050, 2960, 2880, 1660, 1600, 1500, 1470, 1370, 1300, 1030, 1010cm21; H
NMR(CDCl3) d 9.12 (s, NH, D2O exchangeable), 7.45–7.34 (m, 6H), 7.17(dd,
1H, J ¼ 3.50, 3.53Hz), 6.47 (dd, 1H, J ¼ 3.52, 3.51Hz), 5.01 (s, 2H); 13C
NMR(CDCl3) d 78.77, 111.98, 115.66, 128.57, 128.75, 129.24, 135.12,
144.62, 145.62, 157.33. Anal. Calcd. for C12H11NO3: C, 66.35; H, 5.10; N,

Preparation of O-Alkylhydroxamic Acids
737
6.45. Found: C, 66.58; H, 5.22; N, 6.38; Elution solvent for the column ¼ CH2-
Cl2:THF (40:1, v/v); Rf ¼ 0.32 (CH2Cl2:diethyl ether ¼ 9:1, v/v).
N-Hydroxybenzamide (3i). Colorless solid; M.p. 1028C; IR (KBr) 3350,
3075, 2825, 1660, 1620, 1580, 1520, 1460, 1310, 1240 cm21
;
1H
NMR(DMSO-d6) d 11.23 (s, NH, D2O exchangeable), 9.05(s, OH, D2O
exchangeable), 7.78–7.74 (m, Ar-2H), 7.53–7.42 (m, Ar-3H); 13C
NMR(DMSO-d6) d 126.81, 128.31, 131.08, 136.57, 164.18. Anal. Calcd. for
C7H7NO2: C, 61.31; H, 5.14; N, 10.21. Found: C, 61.25; H, 5.34; N, 10.48;
Elution solvent for the column ¼ ethyl acetate:n-hexane (1:1, v/v);
Rf ¼ 0.1 (ethyl acetate:n-hexane ¼ 1:1, v/v).
N-Benzyloxypentanamide (3j). Colorless liquid; IR (KBr) 3200, 2980,
2880, 1660, 1500, 1460, 1370, 1270, 1210, 1100, 1050, 970, 910, 750 cm21
;
1H NMR(CDCl3) d 9.37 (s, NH, D2O exchangeable), 7.36 (s, Ar-5H), 4.87
(s, 2H), 2.05(t, 2H, J ¼ 7.07 Hz), 1.63–1.51 (m, 2H), 1.37–1.25 (m, 2H),
0.87(t, 3H, J ¼ 7.29 Hz); 13C NMR(CDCl3) d 13.74, 22.25, 27.49, 33.88,
78.03, 128.48, 128.56, 129.16, 135.44, 171.38. Anal. Calcd for C12H17NO2:
C, 69.54; H, 8.27; N, 6.76. Found: C, 69.74; H, 8.31; N, 6.78; Elution
solvent for the column ¼ CH2Cl2:diethyl ether (10:1, v/v); Rf ¼ 0.20
(CH2Cl2:diethyl ether ¼ 9:1, v/v).
N-Allyloxypentanamide (3k). Colorless liquid; IR (KBr) 3200, 3100,
2970, 2950, 2880, 1660, 1520, 1470, 1420, 1270, 1190, 1100, 1050,
1
940 cm21; H NMR(CDCl3) d 9.43 (s, NH, D2O exchangeable), 6.04–5.90
(m, 1H), 5.31 (dd, 2H, J ¼ 14.07, 11.93 Hz), 4.38(d, 2H, J ¼ 5.94 Hz),
2.34(t, 2H, J ¼ 7.37 Hz), 1.62(m, 2H), 1.36(m, 2H), 0.92(t, 3H, J ¼
7.30 Hz); 13C NMR(CDCl3) d 13.72, 22.24, 26.89, 33.93, 77.27, 120.34,
132.31, 178.96. Anal. Calcd. for C8H15NO2: C, 61.12; H, 9.62; N, 8.91.
Found: C, 60.99; H, 9.54; N, 9.03; Elution solvent for the column ¼ CH2Cl2:
diethyl ether (7:1, v/v); Rf ¼ 0.33 (CH2Cl2:diethyl ether ¼ 5:1, v/v).
N-Benzyloxycyclohexanecarboxamide (3l). Colorless solid; M.p.
88–898C; IR (KBr) 3200, 3010, 2960, 2880, 1655, 1530, 1460, 1400, 1380,
1
1270, 1220, 1150, 1060, 1020, 960, 750 cm21; H NMR (CDCl3) d 9.14
(s, NH, D2O exchangeable), 7.38–7.27 (m, Ar-5H), 4.87 (s, 2H), 2.01–1.19
(m, 11H); 13C NMR (CDCl3) d 25.54, 29.21, 42.23, 77.92, 128.47, 128.56,
129.22, 135.48, 174.11. Anal. Calcd. for C14H19NO2: C, 72.07; H, 8.21; N,
6.00. Found: C, 71.48; H, 8.11; N, 5.97; Elution solvent for the column ¼ CH2-
Cl2:diethyl ether (10:1, v/v); Rf ¼ 0.30 (CH2Cl2:diethyl ether ¼ 9:1, v/v).
ACKNOWLEDGMENT
This work was supported by a grant from the Korea Science and Engineering
Foundation (KOSEF) to the Environmental Biotechnology National Core
Research Center (grant #: R15-2003-002-01001-0).

738
J.-J. Kim et al.
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