Hydrochloric Acid → HCID 12764424, compound

Participants

Reaction Steps

Iron powder (104 g.) was added to a warm (50° C.) solution of 4-cyclopropanecarbonyl-9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (75 g.) in ethanol (600 ml.) and water (300 ml.). The mixture was heated to reflux, then a solution of concentrated hydrochloric acid (45 ml.), ethanol (90 ml.) and water (90 ml.) was added dropwise. Stirring was continued for four hours after the addition was complete. The mixture was allowed to cool somewhat, then sodium bicarbonate (75 g.) was cautiously added, and the mixture was filtered. The filtrate was concentrated nearly to dryness, and the residue was partitioned between water and chloroform. The chloroform layer was washed with brine, dried, treated with charcoal and stripped of chloroform. Two recrystallizations of the tan foam residue from methanol afforded 4-cyclopropanecarbonyl-9-amino-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (43 g., m.r. 105°-107° C.), the compound of Formula II wherein Q' is cyclopropanecarbonyl. The product appeared to be a methanol solvate. Recrystallization of part of a similarly prepared product from ethyl acetate afforded product free of solvent (m.r. 142°-144° C.).

Provenance & Evidence