Acetyl chloride → N-acetyl-o-toluidine

Participants

Reaction Conditions

Reaction Steps

Ortho toluidine (0.75 moles, 80 g.) was taken in a one liter round bottom flask equipped with a liquid addition funnel and a guard tube. Triethylamine (1.13 moles, 113.77 g.) was added to it in one lot. Above mixture was cooled to 0-5° C. and acetyl chloride was added drop-wise maintaining the temperature below 10° C. After addition of acetyl chloride the cooling was removed and reaction was stirred at 25-28° C. for 3 hours. After the completion of reaction (TLC), the reaction mixture was poured on 500 g. of ice-water, and aqueous layer was extracted with dichloromethane (2×300 mL). The combined dichloromethane extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 113.6 grams solid.

Provenance & Evidence