Dicyclohexylcarbodiimide → 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[(4-methoxy-3-nitrophenyl)acetyl]isoquinoline

Participants

Reaction Steps

A mixture of 4-methoxy-3-nitrophenylacetic acid (1.2 g) and 1-hydroxybenzotriazole (0.95 g) in DMF (30 ml) was stirred at room temperature for 10 min. 1,2,3,4-Tetrahydro-6,7-dimethoxy-isoquinoline (1.1 g) in DMF (20 ml) was then added, followed by dicyclohexylcarbodiimide (1.2 g) and the mixture was stirred at room temperature for 6 h and then filtered. The filtrate was concentrated in vacuo, treated with dilute sodium hydroxyde and extracted with ethyl acetate. The dried organic extract was evaporated to give the title compound (1.6 g) as an oil which crystallised from ethanol as a white solid, MP 175°. IR: Freq CO: 1650 cm-1.

Provenance & Evidence