2-Nitrobenzaldehyde → HCID 178498412, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][OH:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O)([O-:29])=[O:28]>>[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18](=[CH:32][C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[N+:27]([O-:29])=[O:28])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]Participants
Procedure
The reaction of hydroxylamine 82 (0.71 g, 2 mmol) with 2-nitrobenzaldehyde (59) (0.302 g, 2 mmol) afforded, after workup, a yellow oil. The crude product was purified by flash chromatography with 3:4 ethyl acetate/petroleum ether as the eluant to obtain 0.71 g (1.44 mmol. 72%) of 84 as a yellow oil. The oil crystallized from ether/petroleum ether to yield yellow crystalline solid: mp 130°-132° C.; IR (CH2Cl2) 3440, 2980, 1700, 1625, 1575, 1528, 1470, 1345, 1300, 1215, 1105, 905, 852, 775 cm-1 ; 1H NMR (CDCl3) δ 1.13 (d, J=6.2 Hz, 3H), 1.25 (d, J=6.2 Hz, 3H), 2.31 (s, 6H), 3.66 (s, 3H), 4.97 (septet, J=6.2 Hz, 1H), 5.06 (s, 1H), 6.23 (s, 1H), 7.30-9.31 (m, 9H); 13C NMR (CDCl3) δ 19.98, 20.02, 22.47, 22.72, 40.34, 51.67, 67.85, 103.69, 104.37, 120.22, 121.84, 125.25, 125.61, 128.97, 129.17, 130.11, 131.01, 131.08, 134.11, 145.29, 145.82, 148.17, 149.75, 150.35, 167.43, 168.46. Anal. Calcd for C26H27N3O7 : C, 63.28; H, 5.47. Found: C, 63.18; H, 5.26.
Workup
- customafforded
- customThe crude product was purified by flash chromatography with 3:4 ethyl acetate/petroleum ether as the eluant
Sources & evidence
- ORD record
- ord-d92ae744960f4f82ba999bebdd2ea2e4
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758669
Reaction notes
Loading…