2,2,2-trifluoro-1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone → 1-(7-Amino-3,4-dihydroisoquinolin-2(1H)-YL)-2,2,2-trifluoroethanone

Participants

Reaction Steps

7-Nitro-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (15 g, 54.7 mmol) was stirred vigorously in EtOAc (50 mL) with 5% Pd/C (1.5 g) under hydrogen gas (1 atmosphere) for 15 h and then filtered through celite. The filtrate was concentrated under vacuum and yielded 11.2 g (84%) of the tan solid 2-(trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinamine. 1H NMR (400 MHz, DMSO-d6) δ 6.84-6.79 (m, 1H), 6.46-6.40 (m, 1H), 6.35 (m, 1H), 4.95 (s, 2H), 4.56 (s, 2H), 3.76-3.68 (m, 2H), 2.74-2.66 (m, 2H).

Provenance & Evidence