LXXIII.—Derivatives of 2-pyridylhydrazine and 2-quinolylhydrazine

Robert George Fargher, Reginald Furness
1915 Journal of the Chemical Society Transactions  
DURING the course of their experiments on harmine and harmaline Perkin and Robinson (T., 1913, 103, 1974) prepared acetone-2quinolylhydrazine with the object of converting it into 2-methyl-12-quinindole by Fischer's method. It was" found that the quinindole derivative was not produced by heating with hydrochloric acid, zinc chloride, or other condensing agents, because hydrolysis occurred in motst of the experiments. Sinoe it is important to determine whether the process is generally
more » ... e to the pyridine nucleus, we have carried out, a t the suggestion of Professor Perkin, a further series of experiments with derivatives of 2-pyridylhydrazine and 2-quinolylhydrazine. 2-Pyridylhydrazine does not appear to have been previously described, but we have found that it can be readily prepared by the following series of reactions. Pyridine methosulphate is oxidised by potassium f erricyanide to 1-methyl-2-pyridone, which, when heated with phosphorus pentachloride and phosphoryl chloride, yields 2-chloropyridine, and this, on boiling with hydrazine hydrate, is converted into 2-pyridylhydrazine : 2-Pyridylhydrazine melts at 46O, distils a t 140°/20 mm., and
doi:10.1039/ct9150700688 fatcat:f7s6fqyjmjdzfhitznbc4ipvci