Sodium Chloride → HCID 76617925, compound

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butylate (7.6 g) was added slowly to a solution of 5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (14.6 g) in THF (146 mL) cooled to 0° C. After 10 minutes of stirring at 0° C., isopentylnitrite (10.6 g) was slowly added and the reaction mixture was further stirred for 105 minutes at 0° C. The reaction mixture was poured onto half-saturated aqueous NaCl (1200 mL), cooled to 0° C. and dichloromethane (500 mL) was added. The phases were separated, the organic phase was washed with half-saturated aqueous NaCl (1200 mL) and the aqueous layers were extracted with dichloromethane (250 mL) twice. The combined organic layers were dried (MgSO4), concentrated under reduced pressure and dried under high vacuum affording 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (18.4 g, quant.) as a yellow foam, which was used in the next step without further purification.

Provenance & Evidence