Hydrochloric Acid → 7-Amino-1,2,3,4-tetrahydroisoquinoline-1-acetic Acid Methyl Ester Hydrochloride

Participants

Reaction Steps

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester hydrochloride (3.08 g, 10.7 mmol) in a solution of methanol (170 ml) and saturated hydrogen chloride in isopropanol (12 ml) was added 10% Pd--C (0.5 g). The reaction mixture was hydrogenated on a Parr Hydrogenator for 2 h at 50 psi. After the catalyst was removed by filtration, the solvent was concentrated to about 1/5 the volume. Isopropanol (70 ml) was added and the precipitate was collected to afford the title compound as a pale yellow solid (3.10 g, 98%), m.p. 245-6° C. (dec.).

Provenance & Evidence