HCID 20196477, compound → HCID 20196470, compound

Participants

Reaction Steps

A mixture of 3,4-dihydro-4-methyl-7-nitroisoquinoline (14.63 g) and palladium black (4 g) in decahydronaphthalene (170 ml) was refluxed for 6 hours with stirring. The reaction mixture was allowed to stand overnight at ambient temperature, and then filtered and the residue on a filter was washed with chloroform. The filtrate was extracted with 2N hydrochloric acid (70 ml×3). Aqueous sodium hydroxide was added slowly to the combined aqueous layer, under dryice-acetone cooling. The light brown solid was collected, washed with water and dried. The crude product was chromatographed on silica gel column using chloroform as an eluent to give 4-methyl-7-nitroisoquinoline (6.06 g).

Provenance & Evidence