Hydrochloric Acid → N~1~-(3-Methylbutyl)benzene-1,2-diamine

Participants

Reaction Steps

Under cooling, o-nitroacetoanilide (7.2 g, 40 mmol), acetone (28 ml) and powdered potassium hydroxide (2.2 g, 39 mmol) were mixed, to which 1-bromo-3-methylbutane (6.0 g, 40 mmol) was added. After the mixture was refluxed for 5 hours, the precipitate was removed by filtration. The filtrate was concentrated in vacuo and was extracted with chloroform. The occurred oily substance (9.8 g, 39 mmol) was refluxed for concd. hydrochloric acid (39 ml, 390 mmol) for 3 hours. The resultant was extracted with chloroform and concentrated in vacuo to give oily substance (6.4 g, 30.7 mmol), which was added to a mixture of powdered iron (17.1 g, 306 mmol), ethanol (24.5 ml), water (6.2 ml) and concd. hydrochloric acid (0.3 ml, 300 mmol). After the mixture was refluxed for 1.5 hours, the product was treated as in a usual process to obtain the title intermediate.

Provenance & Evidence