3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → 4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid (1S)-[1-(4-methoxy-phenyl)-ethyl]-amide

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-amino-but-2-enoic acid [1-(4-methoxy-phenyl)-ethyl]-amide (10 g), 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (10.4 g) and 5-propylcyclohexane-1,3-dione (6.5 g) in ethanol (150 ml) was stirred at 80° C. for 18 hr. The mixture was concentrated in vacuo. The residue was dissolved in toluene (100 ml) and dichloromethane (50 ml) and evaporated until a precipitated formed. The solid obtained was then crystallized in EtOAc.

Provenance & Evidence