Ammonium Acetate → 6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Participants

Reaction Steps

A total of 59 g (0.16 mol) of 7-bromo-6-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 10 g of 5% palladium on calcium carbonate and 49 g of ammonium acetate in 1 liter of acetic acid was hydrogenated on a Parr shaker for 5 hrs. The reaction was filtered, concentrated, basified to pH 12 with 4N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to yield 40 g of the title compound in the form of an oil.

Provenance & Evidence