Benzaldehyde → HCID 178496300, compound

HRID 845573Notes

Reaction equation

HRID 845573 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].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[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](=[O:22])=[CH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[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 240BenzaldehydeHCID 14183058HCID 14183058, compound

Product 1

HCID 178496300HCID 178496300, compoundYield 86%

Procedure

The reaction of hydroxylamine 55 (0.80 g, 2 mmol) with benzaldehyde (56)(0.21 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 0.85 g (1.72 mmol, 86%) of 67 as a light yellow gum; IR (CH2Cl2) 3440, 2975, 1692, 1620, 1552, 1470, 1298, 1212, 1100 cm-1 ; 1H NMR (CDCl3, 60 MHz) δ 1.16 (t, J=6 Hz, 6H), 2.26 (s, 6H), 3.30 (s, 3H), 3.50 (t, J=5 Hz, 2H), 4.16 (t, J=5 Hz, 2H), 4.70-5.06 (m, 2H), 6.86 (bs, 1H), 7.30-8.46 (m, 10H). Anal. Calcd for C28H32N2O6 : C, 68.29; H, 6.50. Found: C, 68.16; H, 6.31.

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-9b8acbb638f34bbd91c222fa93864bda
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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