Acetic Anhydride → Ethyl 4-(acetylamino)-3-ethoxybenzoate

Participants

Reaction Steps

To a 100 mL round bottom flask were added ethyl 4-amino-3-ethoxybenzoate (1.3 g, 6.2 mmol), TEA (2.6 mL, 18.6 mmol), N,N-dimethylpyridin-4-amine (catalytic), acetic anhydride (0.88 mL, 9.3 mmol) and EtOAc (20 mL). The reaction mixture was stirred at ambient temperature for 3 hours and was then diluted with EtOAc (20 mL) and washed with 5% KOH (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified on a silica gel column eluting with a gradient of EtOAc/hexanes to give the title intermediate (1.1 g) as a pale yellow solid.

Provenance & Evidence