3-Nitrobenzaldehyde → HCID 178498415, compound

HRID 845584Notes

Reaction equation

HRID 845584 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:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=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:33][C:32]3[CH:35]=[CH:36][CH:37]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=3)=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 14183059HCID 14183059, compound

Product 1

HCID 178498415HCID 178498415, compound

Procedure

The reaction of hydroxylamine 82 (0.71 g, 2 mmol) with 3-nitrobenzaldehyde (57) (0.302 g, 2 mmol) afforded, after workup, a light yellow solid. The crude product was recrystallized from ethyl acetate/petroleum ether to obtain 0.71 g (1.44 mmol. 72%) of 83 as a light yellow crystalline solid: mp 149°-151° C.; IR (CH2Cl2) 3440, 2980, 1700, 1622, 1552, 1535, 1475, 1355, 1300, 1215, 1100, 1018, 810 cm-1 ; 1H NMR (CDCl3) δ 1.14 (d, J=6.2 Hz, 3H), 1.25 (d, J=6.2 Hz, 3H), 2.30 (s, 6H), 3.64 (s, 3H), 4.97 (septet, J=6.2 Hz, 1H), 5.08 (s, 1H), 6.37 (s, 1H), 7.32-9.29 (m, 9H); 13C NMR (CDCl3) δ 19.78, 22.47, 22.70, 40.51, 51.58, 67.81, 103.27, 103.99, 119.82, 121.99, 123.79, 125.43, 129.16, 130.24, 131.05, 132.75, 132.94, 134.75, 145.57, 146.11, 148.91, 149.20, 150.56, 167.59, 168.60. Anal. Calcd for C26H27N3O7 : C, 63.28; H, 5.47. Found: C, 63.49; H, 5.47.

Workup

  1. customafforded
  2. customThe crude product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-a859a6797b0d490197f18a6548be1c9e
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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