Hydrochloric Acid → 1-(4-Bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylic acid

Participants

Reaction Steps

Into a 250 milliliter Erlenmeyer flask equipped with a magnetic stirrer and condenser was added 15.0 grams (0.05 mol) of ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate, 150 milliliters of dimethylformamide and 14.0 grams (0.10 mol) of 1-bromo-2-chloroethane. The resulting mixture was stirred at ambient temperature and potassium carbonate (4.0 grams, 0.03 mol) was added at a rate of 1 gram every 30 minutes. After liquid chromatographic analysis showed the ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate peak disappeared, potassium hydroxide (5.0 grams, 0.09 mol) was added until no ethyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylate remained. The reaction mixture was diluted to 300 milliliters with water and acidified with concentrated HCl to a pH of 1 to afford a solid material. The solid was collected on a Buchner funnel and dried under ambient temperature to give 13.65 grams (0.046 mol) of 1-(4-bromo-2-methylphenylaminocarbonyl)cyclopropanecarboxylic acid. The total yield was 91.5 percent based on a 97.6 weight percent liquid chromatographic assay of the starting ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate.

Provenance & Evidence