Dichloromethane → 2-Benzoyl-5-bromo-1-cyano-1,2-dihydroisoquinoline

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 5-bromoisoquinoline (available from Aldrich; 4 g, 19.2 mmol), dichloromethane (DCM) (50 ml), trimethylsilyl cyanide (4.81 ml, 38.5 mmol) and aluminium chloride (15 mg, 0.112 mmol). To the mixture was added benzoyl chloride (4.46 ml, 38.5 mmol) slowly over a period of 5 minutes. The mixture was warmed to 30° C. for 3 h after which time it was treated with water (50 ml) and stirred at room temperature for 30 minutes. The organic layers were collected and washed sequentially with 2N HCl, 2N NaOH and brine. The organic layers were passed through a hydrophobic frit before being concentrated in vacuo to give an orange solid. The solid was triturated with diethyl ether and the slurry filtered. The isolated solid was dried in vacuo to give the title compound as a grey solid (3.9 g).

Provenance & Evidence