UPDATES
4-Chloro-N-hydroxybenzamide (10): White solid; yield:
127.6, 126.4, 34.9; HR-MS (ESI): m/z=186.0317, calcd. for
C8H9ClNO2: 186.0316 [M+H]+..
1
151 mg (88%); mp 190–1918C (Lit.[8a] 193–1948C). H NMR
(400 MHz, DMSO-d6): d=11.24 (s, 1H), 9.05 (s, 1H), 7.71
(d, J=8.0 Hz, 2H), 7.46 (d, J=8.1 Hz, 2H); 13C NMR
(101 MHz, DMSO-d6): d=163.1, 135.9, 131.5, 128.8, 128.5.
Spectroscopic data are in agreement with those reported
earlier.[8b,21]
N-Hydroxy-2-(4-nitrophenyl)acetamide (20): White solid;
yield: 174 mg (89%); mp 149–1508C. IR (KBr): n=3364,
3335, 3209, 3069, 1663, 1626, 1609, 1524, 1497, 1541, 1387,
1310, 1354, 1111, 1045, 982 cmÀ1
;
1H NMR (400 MHz,
DMSO-d6): d=10.74 (s, 1H), 8.92 (s, 1H), 8.18 (d, J=
8.5 Hz, 2H), 7.53 (d, J=8.2 Hz, 2H), 3.46 (s, 2H); 13C NMR
(101 MHz, DMSO-d6): d=165.8, 146.3, 144.1, 130.2, 123.3,
38.9. Spectroscopic data are in agreement with those report-
ed earlier.[24]
4-Cyano-N-hydroxybenzamide (11): White solid; yield:
1
84 mg (52%); mp 174–1758C (Lit.[8b] 173–1748C). H NMR
(500 MHz, DMSO-d6): d=11.45 (s, 1H), 9.26 (s, 1H), 8.00–
7.84 (m, 4H); 13C NMR (101 MHz, DMSO-d6): d=167.7,
142.0, 137.7, 132.87, 123.4, 118.7. Spectroscopic data are in
agreement with those reported earlier.[8b,22]
N-Hydroxy-3-methyl-4-nitrobenzamide (14): White solid;
yield: 151 mg (77%); mp 154–1558C. 1H NMR (400 MHz,
DMSO-d6): d=11.10 (s, 1H), 8.93 (s, 1H), 7.52 (s, 1H), 7.48
(t, J=4.4 Hz, 1H), 7.26 (d, J=4.5 Hz, 1H), 2.28 (s, 3H);
13C NMR (101 MHz, DMSO-d6): d=165.0, 138.3, 133.4,
132.3, 128.9, 128.1, 124.6, 21.6; HR-MS (ESI): m/z=
197.0559, calcd. for C8H9N2O4: 197.0557 [M+H]+.
N-Hydroxy-2-phenoxyacetamide (21): White solid; yield:
145 mg (87%); mp 114–1158C (Lit.[25] 1158C). IR (KBr): n=
3302, 2853, 1682, 1641, 1599, 1558, 1491, 1252, 1238, 1088,
1
1067, 752 cmÀ1; H NMR (400 MHz, DMSO-d6): d=10.75 (s,
1H), 8.90 (s, 1H), 7.24 (t, J=7.7 Hz, 2H), 6.90 (t, J=7.6 Hz,
3H), 4.39 (s, 2H); 13C NMR (101 MHz, DMSO-d6): d=
164.3, 157.8, 129.4, 121.1, 114.6, 65.8. Spectroscopic data are
in agreement with those reported earlier.[26]
2-(Benzylthio)-N-hydroxyacetamide (22): White solid;
yield: 132 mg (67%); mp 109–1108C (Lit.[11] 1118C). IR
(KBr): n=3250, 3086, 3059, 3026, 2957, 2932, 2978, 1641,
N-Kydroxythiophene-3-carboxamide (15): White solid;
yield: 106 mg (74%); mp 133–1348C. IR (KBr): n=3283,
3115, 3098, 3049, 2926, 2758, 1657, 1611, 1570, 1516, 1416,
1
1520, 1495, 1454, 1402, 1047, 980 cmÀ1; H NMR (400 MHz,
1
1395, 1136, 851, 808 cmÀ1; H NMR (400 MHz, DMSO-d6):
DMSO-d6): d=10.56 (s, 1H), 8.91 (s, 1H), 7.44–7.13 (m,
5H), 3.83 (s, 2H), 2.92 (s, 2H); 13C NMR (101 MHz,
DMSO-d6): d=166.5, 138.6, 129.6, 129.0, 127.6, 36.3, 31.9;
HR-MS (ESI): m/z=198.0585, calcd. for C9H12NO2S:
198.0583 [M+H]+. Spectroscopic data are in agreement
with those reported earlier.[27]
d=11.06 (s, 1H), 9.12 (d, J=75.9 Hz, 1H), 8.04 (d, J=
2.9 Hz, 1H), 7.58 (dd, J=5.1, 2.9 Hz, 1H), 7.43 (dd, J=5.0,
1.2 Hz, 1H); 13C NMR (101 MHz, DMSO-d6): d=161.0,
135.9, 128.8, 127.5, 126.8; HR-MS (ESI): m/z=144.0115,
calcd. for C5H6NO2: 144.0114 [M+H]+.
N-Hydroxy-2-(m-tolyl)acetamide (16): White solid; yield:
149 mg (90%); mp 151–1528C. IR (KBr): n=3204, 3034,
2974, 2941, 2887, 1636, 1497, 1541, 1460, 1356, 1059,
N-Hydroxy-2-phenylbutanamide (23): White solid; yield:
161 mg (90%); mp 112–1138C. IR (KBr): n=3207, 3090,
3026, 2928, 2966, 2906, 2877, 1707, 1630, 1527, 1497, 1483,
1
974 cmÀ1; H NMR (400 MHz, DMSO-d6): d=10.59 (s, 1H),
1454, 1462, 1367, 1040, 986, 725, 696 cmÀ1
;
1H NMR
8.78 (s, 1H), 7.22–7.14 (m, 1H), 7.11 (dd, J=7.8, 2.1 Hz,
3H), 3.30 (s, 2H), 2.28 (s, 3H); 13C NMR (101 MHz,
DMSO-d6): d=167.6, 137.1, 135.2, 130.4 (2C), 127.2, 126.3,
37.5, 20.0; HR-MS (ESI): m/z=166.0867, calcd. for
C9H12NO2: 166.0863 [M+H]+.
N-Hydroxy-2-(4-methoxyphenyl)acetamide (17): White
solid; yield: 159 mg (88%); mp153–1548C (Lit.[23] 1548C).
1H NMR (400 MHz, DMSO-d6): d=10.57 (s, 1H), 8.76 (s,
1H), 7.16 (d, J=8.2 Hz, 2H), 6.85 (d, J=8.3 Hz, 2H), 3.72
(s, 3H), 3.19 (s, 2H); 13C NMR (101 MHz, DMSO-d6): d=
167.3, 157.9, 129.8, 127.9, 113.6, 54.9, 38.4. Spectroscopic
data are in agreement with those reported earlier.[10]
(400 MHz, DMSO-d6): d=10.58 (s, 1H), 8.74 (s, 1H), 7.25
(dd, J=9.8, 6.9 Hz, 5H), 3.09 (dd, J=9.0, 6.2 Hz, 1H), 1.97–
1.83 (m, 1H), 1.60 (m, 1H), 0.76 (t, J=7.2 Hz, 3H);
13C NMR (101 MHz, DMSO-d6): d=170.2, 141.3, 128.8,
128.3, 127.2, 50.8, 26.5, 12.8; HR-MS (ESI): m/z=180.1022,
calcd. for C10H14NO2: 180.1019 [M+H]+. Spectroscopic data
are in agreement with those reported earlier.[28]
N-Hydroxy-2,2-diphenylacetamide (24): White solid;
yield: 207 mg (91%); mp172–1738C (Lit.[29] 1728C).
1H NMR (400 MHz, DMSO-d6): d=10.91 (s, 1H), 8.94 (s,
1H), 7.34–7.28 (m, 8H), 7.24 (d, J=6.4 Hz, 2H), 4.70 (s,
1H); 13C NMR (101 MHz, DMSO-d6): d=168.6, 140.6,
129.1, 128.9, 127.4, 54.0. Spectroscopic data are in agreement
with those reported earlier.[30,31]
2-(Benzo[d][1,3]dioxol-5-yl)-N-hydroxyacetamide
(18):
White solid; yield: 178 mg (91%); mp 156–1578C. IR (KBr):
n=3204, 3024, 2943, 2901, 1636, 1547, 1503, 1489, 1447,
1418, 1377, 1360, 1250, 1202, 1190, 1055, 1038, 978, 926,
N-Hydroxyisobutyramide (25): White solid; yield: 53 mg
1
(51%); mp 114–1158C (Lit.[8e] 1148C). H NMR (400 MHz,
1
866 cmÀ1; H NMR (400 MHz, DMSO-d6): d=10.57 (s, 1H),
DMSO-d6): d=10.29 (s, 1H), 8.57 (s, 1H), 2.17 (hept, J=
6.8 Hz, 1H), 0.93 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz,
DMSO-d6): d=173.1, 31.1, 19.4. Spectroscopic data are in
agreement with those reported earlier.[8e]
N-Hydroxy-4-phenylbutanamide (26): White solid; yield:
154 mg (86%); mp 73–748C (Lit.[32] 71–728C). 1H NMR
(400 MHz, DMSO-d6): d=10.32 (s, 1H), 8.65 (s, 1H), 7.24
(t, J=7.2 Hz, 2H), 7.12 (d, J=7.2 Hz, 3H), 2.49 (t, J=
7.7 Hz, 2H), 1.92 (t, J=7.4 Hz, 2H), 1.72 (q, J=7.4 Hz,
2H); 13C NMR (101 MHz, DMSO-d6): d=168.9, 141.6,
128.3, 125.8, 39.5, 34.6, 31.8, 26.9. Spectroscopic data are in
agreement with those reported earlier.[33,34]
8.78 (s, 1H), 6.82 (d, J=8.1 Hz, 2H), 6.70 (d, J=8.0 Hz,
1H), 5.97 (s, 2H), 3.18 (s, 2H); 13C NMR (101 MHz,
DMSO-d6): d=167.1, 147.0, 145.8, 129.6, 121.9, 109.3, 107.9,
100.7, 38.9; HR-MS (ESI): m/z=196.0607, calcd. for
C9H10NO4: 196.0604 [M+H]+.
2-(3-Chlorophenyl)-N-hydroxyacetamide
(19):
White
solid; yield: 170 mg (92%); mp 152–1538C. IR (KBr): n=
3190, 3013, 2903, 1638, 1599, 1574, 1543,1474, 1433, 1352,
1080, 1057, 978, 866, 800, 764 cmÀ1 1H NMR (400 MHz,
;
DMSO-d6): d=10.66 (s, 1H), 8.86 (s, 1H), 7.32 (dd, J=7.3,
4.5 Hz, 3H), 7.21 (d, J=7.3 Hz, 1H), 3.30 (s, 2H); 13C NMR
(101 MHz, DMSO-d6): d=166.4, 138.5, 132.7, 130.0, 128.7,
Adv. Synth. Catal. 0000, 000, 0 – 0
6
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
These are not the final page numbers!