2-Chlorobenzaldehyde → HCID 178496302, compound

HRID 845577Notes

Reaction equation

HRID 845577 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][CH:36]=[CH:35][C:32]=1[CH:33]=O>>[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:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[Cl:30])=[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 69962-ChlorobenzaldehydeHCID 14183058HCID 14183058, compound

Product 1

HCID 178496302HCID 178496302, compoundYield 80%

Procedure

The reaction of hydroxylamine 55 (1.97 g, 5 mmol) with 2-chlorobenzaldehyde (61) (0.70 g, 5 mmol) afforded, after workup, a light yellow oil. The crude product was purified by flash chromatography with 3:5 ethyl acetate/petroleum ether as the eluant to obtain 2.11 g (4.0 mmol, 80%) of 72 as a light yellow gum: IR (CH2Cl2) 3440, 2940, 1690, 1623, 1590, 1550, 1470, 1295, 1202, 1100; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.25 (s, 6H), 3.30 (s, 3H), 3.54 (t, J=4.8 Hz, 2H), 4.16 (m, 2H), 4.93 (septet, J=6.2 Hz, 1H), 5.07 (s, 1H), 6.87 (s, 1H), 7.27-9.45 (m, 9H); 13C NMR (CDCl3) δ 19.69, 19.84, 22.49, 22.72, 40.43, 59.36, 63.40, 67.70, 71.18, 103.32, 104.11, 120.08, 122.09, 127.76, 128.94, 129.04, 129.76, 130.22, 130.94, 131.28, 132.16, 134.30, 145.57, 146.32, 149.83, 150.49, 167.51, 167.99. Anal. Calcd for C28H31N2O6Cl: C, 63.81; H, 5.88. Found: C, 63.51; H, 6.02.

Workup

  1. customafforded
  2. customThe crude product was purified by flash chromatography with 3:5 ethyl acetate/petroleum ether as the eluant

Sources & evidence

ORD record
ord-e2e7824eb3b547a3a7abea2c5d65a158
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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