HCID 10910721, compound → 1-Propanone, 1-(2-aminophenyl)-2,2-dimethyl-

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Reaction Steps

To a solution of 1-(2-nitrophenyl)-2,2-dimethylpropan-1-one (5 g, 24 mmol) (ref: Aus. J. Chem., 34, 1875-8 (1981)) in ethanol (100 ml) was added 10% palladium on carbon (0.5 g, 10% (w/w)) in hydrochloric acid (5 ml of a 5M solution). The mixture was hydrogenated at 25 psi for 20 min, then the catalyst was filtered off and washed with methanol. The solvents were evaporated in vacuo. The oily residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml). The organic phase was separated, washed with brine (25 ml), dried (Na2SO4) and evaporated. Trituration of the solid with diethyl ether afforded the title compound as a colourless solid (3 g, 70%). 1H NMR (250 MHz, CDCl3) δ 1.38 (9H, s), 5.64 (2H, brs), 6.60-7.30 (4H, m).

Provenance & Evidence