3-Nitrobenzaldehyde → HCID 178496308, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][OH:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9].[N+:30]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=O)([O-:32])=[O:31]>>[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21](=[CH:36][C:35]3[CH:38]=[CH:39][CH:40]=[C:33]([N+:30]([O-:32])=[O:31])[CH:34]=3)=[O:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]Participants
Procedure
The reaction of hydroxylamine 55 (0.80 g, 2 mmol) with 3-nitrobenzaldehyde (57) (0.302 g, 2 mmol) afforded, after workup, a yellow solid. The crude product was recrystallized from dichloromethane-petroleum ether to afford 0.82 g (1.53 mmol, 77%) of 68 as a light yellow crystalline solid: mp 175°-178° C.; IR (CH2Cl2) 3440, 2980, 1695, 1620, 1550, 1532, 1470, 1350, 1295, 1210, 1100, 905, 810 cm-1 ; 1H NMR (CDCl3) δ 1.11 (d, J=6.2 Hz, 3H), 1.23 (d, J=6.2 Hz, 3H), 2.29 (s, 6H), 3.32 (s, 3H), 3.58 (t, J=4.8 Hz, 2H), 4.20 (m, 2H), 4.94 (septet, J=6.2 Hz, 1H), 5.09 (s, 1H), 6.46 (s, 1H), 7.32-9.28 (m, 9H); 13C NMR (CDCl3) δ 19.38, 19.48, 21.97, 22.20, 40.09, 58.82, 62.85, 67.28, 70.72, 102.95, 103.74, 119.45, 121.46, 123.39, 124.88, 128.68, 129.76, 130.68, 132.25, 132.37, 134.13, 144.77, 145.57, 148.44, 148.61, 149.94, 166.96, 167.43; mass spectrum, m/e (relative intensity) 537 (M+, 0.1), 296 (100), 254 (66.6), 196 (67.2), 150 (15.8), 59 (20.6), 43 (21.1), 28 (73.7). Anal. Calcd for C28H31N3O8 : C, 62.57; H, 5.77. Found: C, 62.74; H, 5.60.
Workup
- customafforded
- customThe crude product was recrystallized from dichloromethane-petroleum ether
Sources & evidence
- ORD record
- ord-307abedba8884f24ac57f79965a87e5b
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758669
Reaction notes
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