3-Bromo-4-hydroxybenzaldehyde → 4-(3-Bromo-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

HRID 909384Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[CH3:11]/[C:12](/[NH2:16])=[CH:13]\[C:14]#[N:15].[CH2:17]([CH:20]1[CH2:25][C:24](=[O:26])[CH2:23][C:22](=O)[CH2:21]1)[CH2:18][CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:23]3[C:24](=[O:26])[CH2:25][CH:20]([CH2:17][CH2:18][CH3:19])[CH2:21][C:22]=3[NH:16][C:12]([CH3:11])=[C:13]2[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

Reactant 3

HCID 763083-Bromo-4-hydroxybenzaldehyde

HCID 27372245-Propylcyclohexane-1,3-dione

HCID 53247203-Aminocrotonitrile

Product 1

HCID 674122614-(3-Bromo-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

Procedure

The reaction of 3-bromo-4-hydroxy-benzaldehyde (13.07 g) with 3-aminocrotonitril (5.34 g) and 5-propylcyclohexane-1,3-dione (10.02 g) was performed according to the method described in example 1a. Yield: 20.25 g. MS-ESI: [M+H]+=401/403

Sources & evidence

ORD record: ord-85b90a07053d47d69bbd7eeb014e16de
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017782B2

Reaction notes

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