6-Nitroindan-1-one → 6-amino-2,3-dihydro-1H-inden-1-one

Participants

Reaction Steps

A mixture of 6-nitroindan-1-one (1 part) and Raney-Ni in EtOH is treated with hydrogen (60 psi) for several hours. The catalyst is removed and the solvent evaporated to give 6-aminoindan-1-one. A solution of the aminoindanone (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of an acyl chloride (1.2 parts) and the reaction is stirred overnight. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give the 6-carboxamido-indan-1-one. A solution of this product (1 part) in a mixture of EtOH and NH3 (5 parts) is treated with hydrogen (60 psi) in the presence of Pd--C-sulfided. After several hours, the catalyst is removed and the solvent evaporated to give 1-amino-6-carboxamido-indane. A solution of the indane (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of a benzoyl chloride (1.2 parts) and the reaction stirred over night. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give the 1-benzamido-6-carboxamido-indane.

Provenance & Evidence