Hydrazine → HCID 178450903, compound

Participants

Reaction Steps

To a slurry of t-butyl(E)-3-(8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepin-4-yl)acrylate (prepared as described in Example 44 of WO94/29275 published Dec. 22, 1994) (0.81 g, 2.2 mmol) in methanol (5 mL) was added anhydrous hydrazine (0.14 g, 4.5 mmol) dropwise via syringe. The resulting bright yellow mixture immediately darkened to an orange color. After 45 minutes of stirring at room temperature, the reaction mixture became a thick yellow-orange slurry which was allowed to stir for an additional 18 hours. The reaction mixture was filtered to give a solid which was recrystallized from ethanol. Very little product was recovered and the filtrate was concentrated and purified with a silica gel plug using ethyl acetate:hexanes (50:50) as the eluent to give an orange oil. This was allowed to crystallize in ethanol at −10° C. for 18 hours, filtered and dried at 100° C. to give the title compound (0.2 g, 25%, m.p. 226.5-228.6° C.).

Provenance & Evidence