Ethyl 2-methyl-2-(4-nitrophenyl)propanoate → Ethyl 2-(4-aminophenyl)-2-methylpropanoate

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Reaction Steps

In 120 ml of ethanol, 20.33 g of the ester obtained above was hydrogenated with 0.3 g of palladium black catalyst. The palladium catalyst was filtered off and the ethanol was distilled off in vacuo. The residue was taken up in 5% hydrochloric acid and washed with ethyl acetate. The separated water layer was neutralized with sodium carbonate and extracted with ethyl acetate. After the ethyl acetate layer was dried over sodium sulfate, the ethyl acetate was distilled off in vacuo and the residue was subjected to silica gel chromatography using chloroform as a solvent to give 8.31 g (0.04 mole, 47% yield) of ethyl 2-(4-aminophenyl)-2-methylpropionate.

Provenance & Evidence