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 1663397Notes

Reaction equation

HRID 1663397 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[CH2:11]([CH:14]1[CH2:19][C:18](=O)[CH2:17][C:16](=[O:21])[CH2:15]1)[CH2:12][CH3:13].[CH3:22]/[C:23](/[NH2:27])=[CH:24]\[C:25]#[N:26]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:17]3[C:16](=[O:21])[CH2:15][CH:14]([CH2:11][CH2:12][CH3:13])[CH2:19][C:18]=3[NH:27][C:23]([CH3:22])=[C:24]2[C:25]#[N:26])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 763083-Bromo-4-hydroxybenzaldehydeHCID 27372245-Propylcyclohexane-1,3-dioneHCID 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-4-hydroxy-benzaldehyde (13.07 g), 5-propylcyclohexane-1,3-dione (10.02 g) and 3-aminocrotonitrile (5.34 g) in ethanol (165 ml) was stirred at 80° C. for 17 h. A precipitate formed, which was collected by filtration. The filtrate was concentrated in vacuo and then triturated with ethyl acetate. The solids were combined and dried in vacuo.

Workup

  1. customA precipitate formed
  2. filtrationwhich was collected by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. customtriturated with ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2aece56549a448f59fdf10c76f7b0c33
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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