Aluminum(III) Chloride → HCID 136016309, compound

Participants

Reaction Steps

A solution of 1.2 g (0.0037 mole) of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-methoxy-2H-1,4-benzodiazepin-2-one (Ib, prepared in Example 30) in 100 mL of 1,2-dichloroethane was stirred with 2.5 g (0.0187 mole) of aluminum trichloride at 42° C. for 8 hours, after which an additional 2.5 g of aluminum trichloride was added. Heating and stirring was continued for another 48 hours after which time an additional 2.5 g of aluminum trichloride was added. After 6 hours, the mixture was cooled and then poured onto ice water. The water was extracted with dichloromethane-methanol-tetrahydrofuran (80:10:10), and the extract washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1.6 g of crude 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq). Purification by silica gel chromatography, eluting with ethyl acetate-methanol (90:10) yielded 1.17 g of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq) (MH+/Z=312) which was of sufficient purity for use in the next step.

Provenance & Evidence