Sodium Hydroxide → 2-Cyano-3-cyclobutyloxy-4,5-dimethoxyaniline

Participants

Reaction Steps

A solution of sodium dithionite (27.6 g, 0.144 mol) in water (100 ml) was added to a solution of 2-cyano-3-cyclobutyloxy-4,5-dimethoxynitrobenzene (4.0 g, 0.0143 mol) and tetra-n-butylammonium chloride (2.33 g, 0.0084 mol) in dichloromethane (100 ml) and the reaction stirred vigorously for 90 minutes. 2N aqueous sodium hydroxide solution (100 ml) and dichloromethane (100 ml) were then added and stirring continued for 5 minutes. The aqueous phase was extracted with further dichloromethane (400 ml) and the combined organic extracts dried (MgSO4), filtered and concentrated under reduced pressure to a volume of 50 ml. Ethereal hydrogen chloride was added and the resulting precipitate filtered and washed with diethyl ether. The solid was then partitioned between 2N aqueous sodium hydroxide (50 ml) and dichloromethane (100 ml) and the organic layer dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound as a yellow oil (2.99 g, 86%). Rf 0.75 (ethyl acetate). MS m/z 266 (MNH4)+.

Provenance & Evidence