Ammonia → HCID 67717348, compound

Participants

Reaction Conditions

Reaction Steps

A sample of methyl 3-(cyanomethyl)benzoate (1.87 g, 0.011 mol) was dissolved in anhydrous CH2Cl2 (100 mL) containing absolute EtOH (15 mL). The mixture was cooled to 0° C. and a stream of HCl gas passed through the solution for 10 min. The mixture was then refrigerated for 6 days. The mixture was transferred to a 500-mL flask and concentrated in vacuo (0.05 mm Hg) at 0° C. to give a white solid. The solid material was dissolved in anhydrous methanol (200 mL) and anhydrous ammonia passed through the solution for 20 min. The mixture was warmed to 50° C. for 18 h. The solution was cooled and filtered to remove solids. The filtrate was concentrated at room temperature in vacuo to give a white foam (2.5 g, quantitative). A portion (ca. 1 g) of the material was dried over toluene to give methyl 3-[(aminoiminomethyl)methyl]benzoate hydrochloride, mp 139°-140° C.

Provenance & Evidence