4-Nitrobenzaldehyde → HCID 178496312, 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:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)([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:37][C:36]3[CH:39]=[CH:40][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=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 4-nitrobenzaldehyde (58) (0.30 g, 2 mmol) afforded, after workup, a yellow oil. The crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant to obtain 0.76 g (1.42 mmol, 71%) of 69 as a yellow oil. The oil crystallized from ethyl acetate-pentane to yield red crystalline solid: mp 148°-150° C.; IR (CH2Cl2) 3435, 29980, 1695, 1620, 1598, 1545, 1520, 1470, 1342, 1215, 1102, 858; 1H NMR (CDCl3) δ 1.08 (d, J=6.2 Hz, 3H), 1.19 (d, J=6.2 Hz, 3H), 2.25 (s, 6H), 3.28 (s, 3H), 3.55 (t, J=4.8 Hz, 2H), 4.16 (m, 2H), 4.92 (septet, J=6.2 Hz, 1H), 5.06 (s, 1H), 6.66 (s, 1H), 7.27-8.51 (m, 9H); 13C NMR (CDCl3) δ 19.78, 19.88, 22.45, 22.68, 40.60, 59.26, 63.36, 67.79, 71.19, 103.34, 104.16, 119.97, 122.05, 124.43, 129.24, 129.84, 131.23, 132.97, 137.03, 145.36, 146.17, 148.45, 149.23, 150.50, 167.46, 167.94. Anal. Calcd for C28H31N3O8 : C, 62.57; H, 5.77. Found: C, 62.76, H, 5.82.
Workup
- customafforded
- customThe crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant
Sources & evidence
- ORD record
- ord-c682c8dbea7f48e6983fc417a6a795a8
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758669
Reaction notes
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