3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile → 3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde

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Reaction Steps

3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde was prepared from 3-chloro-4-cyano-methyl-5,6,7,8-tetrahydroisoquinoline by reduction with diisobutylaluminium hydride following essentially the same procedure as that described in J. Org. chem., 1980, 45, 1354 for the reduction of 3-cyano-2-methoxy-6-methylpyridine. Pmr spectrum (CDCl3 ; δ in ppm): 1.79 (4H,m); 2.47 (3H,s); 2.59-3.18 (4H,m); 10.52 (1H,s).

Provenance & Evidence