Homophthalic anhydride → HCID 12015732, compound

Participants

Reaction Steps

To the solution of homophthalic anhydride (6.80 g, 41.9 mmol) in 70 mL of glacial acetic acid was added 1-methyl-2-(1-methylethyl)hydrazine, dihydrochloride (6.75 g, 41.9 mmol) in 35 mL of pyridine (Rosen, et al., J. Heterocyclic Chem., 1969, 6, 9-12). The solution was refluxed for 12 h, cooled, diluted with water (300 mL), and extracted with chloroform (3×400 mL). The chloroform extract was washed with 10% hydrochloric acid (600 mL) and 5% sodium bicarbonate (600 mL) , dried over magnesium sulfate and concentrated to dryness. The mixture was purified by silica gel chromatography (hexane/ethyl acetate, 3/1) to afford 2,3,4,5-tetrahydro-3-methyl-2-(1-methylethyl)-1H-2,3-benzodiazepin-1,4-dione (5 g, 51%).

Provenance & Evidence