Hydrochloric Acid → 4-Chloro-3-(cyclopropylmethoxy)aniline

Participants

Reaction Conditions

Reaction Steps

1-chloro-2-cyclopropylmethoxy-4-nitro-benzene (2.3 g, 10 mmol) was dissolved in ethanol (30 ml) and water (30 ml), and then sodium dithionite was gradually added thereto. This was stirred at 80° C. for four and half hours. After cooling it to room temperature, an aqueous solution of 5 M hydrochloride (40 ml) was added to the reaction mixture. This was stirred at room temperature for one hour. Then, an aqueous solution (42 ml) of 5 M sodium hydroxide was added, and the solution was alkalinized and extracted with ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 4-chloro-3-cyclopropylmethoxy-phenylamine was obtained as a pale yellow gum-like material (1.4 g).

Provenance & Evidence