Acetohydrazide → 7-Bromo-8-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-bromo-7-fluoro-3,4-dihydroquinoline-2(1H)-thione (122-4; 7.0 g, 0.026 mol) in n-butanol (30 mL) was added acetic hydrazide (4.81 g, 0.065 mol). Reaction mass was warmed at 120° C. for 16 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.88-7.86 (d, J=7.6 Hz, 1H), 7.70-7.67 (d, J=10 Hz, 1H), 3.0-2.94 (m, 4H), 2.67 (s, 3H). MS (M+1): 284.2.

Provenance & Evidence