Carbon Dioxide → Methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate

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Reaction Steps

A 3-necked flask is charged with 3-methyl-5,6,7,8-tetrahydroquinoline (45 g. 0.29 moles) and ether (400 ml). Phenyl lithium solution (330 ml. of a 1 molar solution 0.3 moles in ether is added to the stirred solution at a rate to give gentle reflux. Reflux is maintained for 2 hours. After cooling in an ice-bath CO2 is bubbled through the resulting red solution of 8-lithio-3-methyl-5,6,7,8-tetrahydroquinoline till no further colour change. The mixture is further treated with methanolic HCl as described in Example 24 of copending U.S. Ser. No. 460,265 to give methyl-3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate.

Provenance & Evidence