4-Ethynyl-1,2-dinitrobenzene → 1,2-Benzenediamine, 4-ethynyl- (9CI)

Participants

Reaction Steps

To a rapidly stirred suspension of 4.1 g of powdered zinc in 10 ml of concentrated ammonium hydroxide was added a solution containing 1.2 g (6.3 mmoles) of 3,4-dinitroethynyl benzene dissolved in 10 ml of tetrahydrofuran. The mixture was stirred at room temperature for one-half hour at which time it was filtered by suction and the residue was washed with ether. The filtrate was extracted with ether, and the combined extracts evaporated to dryness. The residual oil was chromatographed on a 1/2 × 4 inch dry quartz column of silica gel. Elution with methylene chloride removed a first band of impurity, while further elution with ethylacetate produced the product. Evaporation of the eluate to dryness yielded 0.5 g (62% yield) of 4-ethynyl-o-phenylenediamine.

Provenance & Evidence