Acetohydrazide → 7-Bromo-6-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521660Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C(O)CCC.O>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:14]([CH3:15])=[N:17][N:18]=[C:7]1[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution 6-bromo-5-fluoro-3,4-dihydroquinoline-2(1H)-thione (146-6; 0.25 g, 0.00096 mol) in n-butanol (10 mL) was added acetic hydrazide (0.177 g, 0.0024 mol). Reaction mass was heated at 120° C. and maintained for overnight. The reaction mixture was cooled, diluted with water (50 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 7.755-7.714 (t, J=8.4 Hz, 1H), 7.487-7.462 (dd, J=1.2 Hz, 1H), 3.034-3.008 (d, J=10.4 Hz, 4H), 2.640 (s, 3H) MS (M+1): 284.0.

Workup

customReaction mass
temperaturemaintained for overnight
temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate (3×30 mL)
washThe combined organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-cdb417d6abed44bcad6c5fa561b7920d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

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