Hydrazine → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

Combined 6-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide (828 mg, 3.25 mmol) and hydrazine (0.510 mL, 16.25 mmol) in isopropanol (10 mL) and heated at 80° C. for 22 h. Cool to 20° C. and after 2 days a white precipitate formed and was collected by filtration, rinsed with isopropanol, and dried under vacuum to give the title compound as its HCl salt (322 mg) as a white solid. A second crop was collected from the filtrate (500 mg). The combined yield was 822 mg (88%). MS m/z 251 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.26 (m, 2H) 1.57 (dd, J=12.9, 1.8 Hz, 2H) 1.75 (dtt, J=14.9, 7.5, 7.5, 3.4, 3.4 Hz, 1H) 3.11 (t, J=6.3 Hz, 2H) 3.19-3.31 (m, 2H) 3.83 (dd, J=11.4, 2.5 Hz, 2H) 4.26 (br. s., 2H) 6.68 (d, J=8.8 Hz, 1H) 7.87 (dd, J=8.8, 2.3 Hz, 1H) 7.97 (s, 1H) 8.18 (t, J=5.7 Hz, 1H) 8.49 (d, J=1.8 Hz, 1H).

Provenance & Evidence