2-Nitrobenzaldehyde → HCID 178496304, compound

HRID 845576Notes

Reaction equation

HRID 845576 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][CH:38]=[CH:37][C:34]=1[CH:35]=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:35][C:34]3[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=3[N+:30]([O-:32])=[O:31])=[O:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]

Participants

3

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 14183058HCID 14183058, compound

Product 1

HCID 178496304HCID 178496304, compound

Procedure

The reaction of hydroxylamine 55 (0.80 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 1:1 ethyl acetate/hexane as the eluant to obtain 0.80 g (1.49 mmol. 75%) of 70 as a yellow oil. The oil crystallized from ether-petroleum ether to yield yellow crystalline solid: mp 114°-116° C.; IR (CH2Cl2) 3440, 2980, 1700, 1625, 1575, 1528, 1470, 1345, 1300, 1215, 1105, 905, 852, 775 cm-1 ; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.23 (d, J=6.2 Hz, 3H), 2.29 (s, 6H), 3.31 (s, 3H), 3.56 (t, J=4.8 Hz, 2H), 4.19 (m, 2H), 4.93 (septet, J=6.2 Hz, 1H), 5.07 (s, 1H), 6.54 (s, 1H), 7.30-9.25 (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; mass spectrum, m/e (relative intensity) 522 (0.2), 518 (10.8), 386 (13.3), 326 (22.5), 296 (100), 254 (53.4), 196 (44.7), 121 (18.9). Anal. Calcd for C28H31N3O8 : C, 62.57; H, 5.77. Found C, 62.72; H, 5.80.

Workup

  1. customafforded
  2. customThe crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant

Sources & evidence

ORD record
ord-0c0dd9ca651648c99c2781b2ed1f9931
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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