Synthesis of acylhydrazines and, symmetrical and asymmetrical…
CH2, 2 s, 4H), 6.79–7.25 (ArH, m, 5H), 9.59, 9.63 (2 NH, 2 s, 2H); 13C NMR d
57.7 (OMe), 66.2, 69.7 (CH2), 115.9, 122.5, 129.6, 159.3 (aromatic carbons), 169.1,
172.2 (CO). Anal. Calcd for C11H14N2O4: C, 55.46; H, 5.92; N, 11.76. Found: C,
55.41; H, 6.03; N, 11.70.
2-(4-Chlorophenoxy)-N0-(2-(2,4-dichlorophenoxy)acetyl)acetohydrazide (20) White
1
solid. mp: 146–148 °C. IR (KBr) cm-1: 1636 (CO), 3217 (NH); H NMR d 4.69,
4.80 (2 CH2, 2 s, 4H), 6.90–7.45 (ArH, m, 7H), 9.50, 10.10 (2 NH, 2 s, 2H); 13C
NMR d 65.6, 65.9 (CH2), 115.5, 117.2, 125.7, 127.1, 128.4, 128.7, 129.2, 130.8,
153.5, 157.4 (aromatic carbons), 169.0, 174.1 (CO). Anal. Calcd for C16H13Cl3-
N2O4: C, 47.61; H, 3.25; N, 6.94. Found: C, 47.55; H, 3.13; N, 6.86.
2-(2,4-Dichlorophenoxy)-N0-(2-methoxyacetyl)acetohydrazide (21) White solid.
1
mp: 77–79 °C. IR (KBr) cm-1: 1637 (CO), 3225 (NH); H NMR d 3.44 (OMe,
s, 3H), 4.14, 4.75 (2 CH2, 2 s, 4H), 6.71–7.34 (ArH, m, 3H), 9.15, 9.37 (2 NH, 2 s,
2H); 13C NMR d 58.8 (OMe), 65.9, 69.0 (CH2), 117.3, 125.3, 128.5, 128.8, 130.8,
153.3 (aromatic carbons), 168.0, 171.0 (CO). Anal. Calcd for C11H12Cl2N2O4: C,
43.02; H, 3.94; N, 9.12. Found: C, 43.15; H, 4.11; N, 9.20.
2-(Naphthalen-2-yloxy)-N0-(2-phenoxyacetyl)acetohydrazide (22) White solid.
1
mp: 142–144 °C. IR (KBr) cm-1: 1650 (CO), 3216 (NH); H NMR d 4.60, 4.72
(2 CH2, 2 s, 4H), 6.96–7.87 (ArH, m, 12H), 9.65, 9.74 (2 NH, 2 s, 2H); 13C NMR d
64.0, 65.3 (CH2), 109.9, 115.7, 117.6, 121.5, 124.0, 127.2, 127.3, 128.7, 129.4,
129.5, 131.1, 135.2, 156.1, 159.2 (aromatic carbons), 168.7, 175.6 (CO). Anal.
Calcd for C20H18N2O4: C, 68.56; H, 5.18; N, 8.00. Found: C, 68.64; H, 5.31; N,
7.92.
2-(4-Chlorophenoxy)-N0-(2-(naphthalen-2-yloxy)acetyl)acetohydrazide (23) White
solid. mp: 146–148 °C. IR (KBr) cm-1: 1638 (CO), 3246 (NH); 1H NMR
d
4.63, 4.80 (2 CH2, 2 s, 4H), 6.85–7.56 (ArH, m, 11H), 9.49, 9.63 (2 NH, 2 s, 2H);
13C NMR d 60.4, 65.4 (CH2), 110.0, 116.0, 117.6, 124.0, 127.1, 127.2, 127.3,
128.8, 129.3, 129.4, 131.1, 135.2, 156.0, 157.2 (aromatic carbons), 168.7, 174.3
(CO). Anal. Calcd for C20H17ClN2O4: C, 62.42; H, 4.45; N, 7.28. Found: C, 62.51;
H, 4.58; N, 7.23.
2-(2,4-Dichlorophenoxy)-N0-(2-(naphthalen-2-yloxy)acetyl)acetohydrazide (24) White
1
solid. mp: 170–172 °C. IR (KBr) cm-1: 1643 (CO), 3225 (NH); H NMR d 4.72,
4.81 (2 CH2, 2 s, 4H), 6.79–8.00 (ArH, m, 10H), 9.96, 9.97 (2 NH, 2 s, 2H); 13C
NMR d 65.6, 65.9 (CH2), 117.2, 117.7, 123.9, 125.6, 127.1, 127.2, 127.3, 127.4,
128.5, 128.6, 128.7, 129.3, 130.8, 131.0, 135.0, 156.0 (aromatic carbons), 168.6,
175.5 (CO). Anal. Calcd for C20H16Cl2N2O4: C, 57.30; H, 3.85; N, 6.68. Found: C,
57.25; H, 3.94; N, 6.71.
2-Methoxy-N0-(2-(naphthalen-2-yloxy)acetyl)acetohydrazide (25) White solid.
mp: 158–160 °C. IR (KBr) cm-1: 1649 (CO), 3254 (NH); 1H NMR d 3.36
(OMe, s, 3H), 4.16, 4.80 (2 CH2, 2 s, 4H), 7.05–7.75 (ArH, m, 7H), 9.35, 9.94 (2
NH, 2 s, 2H); 13C NMR d 58.8 (OMe), 65.3, 69.7 (CH2), 109.7, 117.8, 124.4,
127.0, 127.3, 128.8, 129.4, 131.1, 135.1, 156.3 (aromatic carbons), 168.8, 171.7
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