Sodium Hydroxide → 1-amino-3-methyl-N-phenyl-1H-pyrrole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

In a three-necked flask it was placed aqueous solution of sodium hydroxide (32%, 95 mL, 665 mmol), ammonium hydroxide solution (8M, 31 mL, 250 mmol), ammonium chloride (10.7 g, 200 mmol) and Aliquat 336 (1.34 g, 3.3 mmol). Afterwards, a solution of 3-methyl-N-phenyl-1H-pyrrole-2-carboxamide (6.6 g, 33.2 mmol) dissolved in 140 mL diethyl ether and 70 mL methyl tert-butyl ether was added and the mixture was cooled at 0° C. affording a suspension. Over this suspension, a 10% aqueous solution of sodium hypochlorite (10%, 224 mL, 300 mmol) was added dropwise over 60 min with vigorous stirring. The reaction mixture was stirred at room temperature overnight. The reaction crude was diluted with ethyl acetate until no suspended material was observed. The layers were separated and the organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduce pressure to give 7.54 g (90% yield) of the title compound that was used in the next step without any further purification.

Provenance & Evidence