Hydrochloric Acid → 7-Amino-5-(4-methoxybenzyl)-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one

Participants

Reaction Conditions

Reaction Steps

Aqueous HCl 3N (18.0 mL) was added to a solution of 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (10.9 g.) in methanol (150.0 mL). Pd/C (10% weight, 1.08 g) was added to the reaction mixture and the system was stirred under 10 bar H2 at 50° C. for 18 hours. After exchanging H2 for Ar, the reaction mixture was filtered, water (150 mL) was added and methanol was removed under reduced pressure. The aqueous phase was extracted with EtOAc (50.0 mL), the organic phase was washed with water (50.0 mL) and the aqueous phases were extracted separately with the same portion of EtOAc (30.0 mL). Dichloromethane (100.0 mL) was added to the combined aqueous phases and aqueous NaOH 0.9 M (65.5 mL) was added slowly to bring the aqueous phase to pH=ca. 7. After 10 minutes of stirring, the phases were separated; the aqueous phase was extracted with dichloromethane (50.0 mL). The combined organic phases were dried (MgSO4) and concentrated under reduced pressure yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (9.7 g, 91%) as yellow oil.

Provenance & Evidence