Methanol → 4-Chloro-2-fluoro-5-(diisopropylaminomethyl)aniline

Participants

Reaction Steps

A mixture of 0.72 g (0.0021 mole) of N,N-diiso-propyl-2-chloro-4-fluoro-5-diacetylaminobenzylamine, 1 g (0.018 mole) of potassium hydroxide, 20 ml of methanol, and 5 ml of water was refluxed for six hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether and was washed with water. The aqueous washes were combined and extracted with methylene chloride. These extracts were combined with the diethyl ether solution. This mixture was dried, filtered, and the solvents were evaporated under reduced pressure, yielding 0.50 g of 4-chloro-2-fluoro-5-(diisopropylaminomethyl)aniline. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence