Carbon Dioxide → 8-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

Participants

Reaction Steps

To a solution of 3-methyl-5,6,7,8-tetrahydroquinoline (10 g) in anhydrous ether (50 ml) was added dropwise with stirring under nitrogen a 1.67 molar solution of methyllithium (40 ml.). The stirring was continued for 1/2 hour then the dark red solution of 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline was treated with a brisk stream of CO2 gas until the suspension became pale yellow. The resulting 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid lithium salt was processed in the manner described in copending application U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Provenance & Evidence