Ammonia → HCID 136388363, compound

Participants

Reaction Steps

2Cyano-6-hydroxybenzofuran (Rene, L.; Buisson, J.-P.; Royer. R. Reaction induites par le chlorhydrate de pyridine. XVI. -Sur la desalcoylation des derives Bz-methoxyles de nitriles et amides coumariliques. Bull. Soc. Chim. 1974, 475-476; 1.45 g, 9.11 mmol) was added to a cooled, saturated methanol-HCl solution (10 mL) and the mixture was stirred for 20 h at ambient temperature. The reaction mixture was concentrated in vacuo to give a solid. The solid was suspended in anhydrous methanol (40 mL) and gaseous NH3 was introduced into the mixture at 50° C. for 3 h to give a homogenous solution. The solvent was evaporated in vacuo, and the resulting solid was suspended in methanol (10 mL) and then treated with a saturated solution of NaHCO3 (30 mL). The precipitate was collected by filtration, washed with water (15 mL) and then dried in vacuo over P2O5 for 3 h. The solid (1.48 g) was suspended in 5 mL of methanol and then treated with methanesulfonic acid (1.1 g, 11.5 mmol). The precipitated material was recrystallized from methanol to give 1.62 g (65%) of 2-amidino-6-hydroxybenzofuran methanesulfonate as a brown solid, mp 253-254° C.

Provenance & Evidence