1,2,3,4-Tetrahydro-1-methylquinoline → 1,2,3,4-Tetrahydroquinoline

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Reaction Steps

1-methyl-6-nitroso-1,2,3.4-tetrahydroquinoline hydrochloride ##STR25## The title compound is prepared from 1-methyl1,2,3,4-tetrahydroquinoline (obtained from 1,2,3,4tetrahydroquinoline by heating with trimethylphosphate (according to Huisgen et al., Chem. Ber. 92, 203 (1959)). The crude product is produced in the usual manner analogous to Examples 10 and 11 and purified on silica gel 60 (Merck) with isopropanol/n-butylacetate/water=5:3:2. The title compound is obtained by dissolving this in acetone after addition of ethereal hydrochloric acid, m.p. 123°-124° C. (decomp.), TLC: silica gel 60, mobile phase: isopropanol/n-butylacetate/water=5:3:2, Rf =0.7.

Provenance & Evidence