Acetic Acid → 6-Methylquinoline-2-carboxylic acid

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Reaction Steps

The resulting (±) 1-benzoyl-2-cyano-1,2-dihydro-6-methylquinoline thus obtained (155.2 g) was added to acetic acid (170 ml) and 48% hydrobromic acid (170 ml) and this mixture was stirred and refluxed for 0.5 hours. After cooling to room temperature, the solid was collected by filtration and then stirred in water (1000 ml) at 80°-90° while concentrated ammonium hydroxide was added until a pH of 8-9 was obtained. After cooling to 50°, acetic acid was added until a pH of 4-5 was reached. The 6-methyl-2-quinolinecarboxylic acid was collected by filtration and then recrystallized from acetic acid; yield 87 g, m.p. 208° (dec).

Provenance & Evidence