t-Butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)carbamate → t-Butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate

Participants

Reaction Steps

A mixture of t-butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)-carbamate (3.72 g, 0.01 mol), absolute ethanol (150 mL) and 10% palladium on carbon (0.60 g) was hydrogenated (50 lb hydrogen pressure) for 18 hours. The mixture was filtered through celite and the solvent removed. The residual foam was partitioned between ethyl acetate and 1 N sodium hydroxide, and the ethyl acetate phase was evaporated under reduced pressure to give 2.72 g of t-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate (compound XXXII) as an oil.

Provenance & Evidence