Hydrazine → HCID 49806738, compound

Participants

Reaction Steps

To a solution of the product from Step F of Example 6, (190 mg, 0.51 mmol) in ethanol (15 mL) was added hydrazine (1 mL, 20.6 mmol) and 10% Pd/C (100 mg). The reaction mixture was heated at reflux for 1 hour. The mixture was then filtered through celite and the celite bed was washed with methanol. The filtrate was concentrated and purified by column chromatography (silica gel, 1% to 5% MeOH/CH2Cl2) to provide 4-(4-Chloro-phenyl)-7-(pyridazin-3-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline (99 mg, 57%): 1H NMR (CDCl3, 500 MHz) δ 9.15 (dd, J=4.9, 1.6 Hz, 1H), 8.05 (d, J=1.3 Hz, 1H), 7.83 (dd, J=8.6, 1.6 Hz, 1H), 7.69 (dd, J=8.1, 1.8 Hz, 1H), 7.53 (dd, J=8.6, 4.9 Hz, 1H), 7.29-7.26 (m, 2H), 7.08-7.05 (m, 2H), 6.98 (d, J=8.1 Hz, 1H), 4.35-4.33 (m, 1H), 4.19 (dd, J=7.9, 5.8 Hz, 1H), 3.49 (dd, J=12.8, 5.5 Hz, 1H), 3.02 (dd, J=12.8, 8.3 Hz, 1H), 1.59 (d, J=6.7 Hz, 3H). ESI MS m/z=336 [M+H]+.

Provenance & Evidence