Methanol → HCID 12640161, compound

Participants

Reaction Steps

To the stirred mixture of 8 g of sodium borohydride and 350 ml of methanol, cooled to -2°, the solution of 20 g of 5-(m-chlorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester in 60 ml of dimethylformamide sufficiently warm for dissolution is added all at once and the container of the latter is washed with 15 ml dimethylformamide and 20 ml methanol containing 0.5 g of sodium borohydride. The mixture warms to about 20°, is cooled to 0° for 40 minutes and stirred at 25° for 15 minutes. It is cooled again to 0° and 9 ml of 12 N hydrochloric acid, 2 ml of acetic acid and 200 ml of ice water are added in this order. The resulting solution is diluted with crushed ice to about 1,000 ml, extracted with ethyl acetate and diethyl ether, the extract dried and evaporated. The residue is first recrystallized from diethyl ether/hexane and then from ethyl acetate/diethyl ether, to yield the 5-(m-chlorobenzylamino)-pyridine-2-carboxylic acid methyl ester of the formula ##STR9## melting at 111°-113°.

Provenance & Evidence