Dimethylformamide → HCID 23128075, compound

Participants

Reaction Steps

A mixture of 3-allyloxy-7-fluoro-1-methyl-4quinolone, obtained as described in Example 8a, (2.3 g), potassium cyanide (1.0 g), 18-crown-6 ether (5.0 g) and dimethylformamide (200 ml) was stirred at 95° for 2 days. After cooling to ambient temperature, the mixture was poured into water (600 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were washed with water (2×200 ml), dried over magnesium sulphate and the solvent was removed by distillation. The residue was triturated with diethyl ether (50 ml) and the resultant solid added to a mixture of potassium cyanide (1.0 g), 18-crown-6 ether (5.0 g) and dimethylformamide (200 ml). The resultant solution was stirred at 140° for 16 hours and then allowed to cool to 60°. The solvent was removed under reduced pressure at 60° and the residue was partitioned between water (100 ml) and dichloromethane ( 200 ml). The dichloromethane solution was dried over magnesium sulphate and filtered through silica gel (30 g). The filter bed was washed with dichloromethane (5×100 ml) and the combined filtrate and washings were evaporated to give crude 3-allyloxy-7-cyano 1-methyl-4-quinolone.

Provenance & Evidence