Hydrochloric Acid → Formamide, N-(2-acetylphenyl)-N-methyl-

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Reaction Steps

A mixture of acetic anhydride (147.2 ml) and formic acid (98%, 100.3 ml) was stirred at 50°-60° for 110 minutes and then cooled to ambient temperature. 2'-(Methylamino)acetophenone (100 g) was added in portions over a period of 30 minutes whilst maintaining the temperature below 30°. The mixture was stirred at ambient temperature for 90 minutes and then cooled to 0°. Water (512 ml) was added over a period of 20 minutes, followed by aqueous sodium hydroxide (specific gravity 1.5, 288 ml) added over a period of 85 minutes whilst maintaining the temperature below 10°. The reaction mixture was transferred to a separating funnel, dichloromethane (200 ml) was added, followed by hydrochloric acid (2M) to pH 9, and the dichloromethane layer separated. The aqueous layer was further extracted with dichloromethane (2×200 ml). The combined dichloromethane extracts were washed with aqueous sodium chloride (6M, 200 ml) and then dried over magnesium sulphate to give a solution of 2'-acetyl-N-methylformanilide.

Provenance & Evidence