N-Methylaniline → HCID 178485594, compound

Participants

Reaction Steps

To a suspension of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]-benzazepine-4,10(1H,9H)-dione (500 mg, 1.72 mmol) (compound of Example 9) in carbon tetrachloride (5 mL) was added phosphorus pentachloride (358 mg, 1.72 mmol). The mixture was stirred for 17 hours, filtered and washed with carbon tetrachloride (3×10 mL). To the residue was added N-methylaniline (190 μL, 1.72 mmol) and dioxane (7 mL). The resulting mixture was stirred 17 hours. To this mixture was added water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (3×100 mL). The organic layers were combined and concentrated by rotary evaporation to 50 mL. The insoluble material was removed by filtration and the organic solution was preabsorbed onto silica gel and purified by flash chromatography eluting with chloroform and chloroform:2-propanol (99:1, 98:2-90:10). The product fractions were combined and concentrated by rotary evaporation to give the title compound as a light yellow solid (100 mg, 15.2%, m.p. 308° C.).

Provenance & Evidence