4-Chlorobenzaldehyde → HCID 178496306, compound

HRID 845578Notes

Reaction equation

HRID 845578 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].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1>>[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][C:31]([Cl:30])=[CH:32][CH:33]=3)=[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 77264-ChlorobenzaldehydeHCID 14183058HCID 14183058, compound

Product 1

HCID 178496306HCID 178496306, compoundYield 75%

Procedure

The reaction of hydroxylamine 55 (1.98 g, 5 mmol) with 4-chlorobenzaldehyde (62) (0.70 g, 5 mmol) afforded, after workup, a light yellow oil. The crude product was purified by flash chromatography with 1:1 ethyl acetate/petroleum ether as the eluant to obtain 1.97 g (3.74 mmol, 75%) of 73 as a light yellow gum: IR (CH2Cl2) 3440, 2980, 1700, 1625, 1590, 1550, 1475, 1300, 1215, 1110, 910, 840; 1H NMR 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.26 (s, 6H), 3.31 (s, 3H), 3.56 (t, J=4.8 Hz, 2H), 4.18 (m, 2H), 4.93 (septet, J=6.2 Hz, 1H), 5.06 (s, 1H), 6.79 (s, 1H) 7.28-8.33 (m, 9H); 13C NMR (CDCl3) δ 19.77, 19.89, 22.48, 22.71, 40.52, 59.32, 63.35, 67.74, 71.21, 103.29, 104.13, 119.97, 122.02, 129.05, 129.52, 129.81, 130.85, 134.35, 136.94, 145.43, 146.25, 149.25, 150.39, 167.56, 168.01. Anal. Calcd for C28H31N2O6Cl; C, 63.81; H, 5.88. Found: C, 63.86; H, 5.84.

Workup

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

Sources & evidence

ORD record
ord-429c8c4a2b5043f3aa95f9acb93f8c82
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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