Acetic Anhydride → 8-Acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

6-Benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline 1-oxide (1.62 g, 5.44 mmol) was dissolved in acetic anhydride (7.7 mL, 81.6 mmol), and the reaction mixture was stirred at 60° C. for 2 h under nitrogen. After this time, the solvent was removed under vacuum to yield a residue, which was dissolved in methylene chloride. The resulting solution was washed sequentially with water, saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to obtain the title compound (1.73 g, 93%) as a brown oil. HPLC/MS [M+H]+, 341.

Provenance & Evidence