Acetohydrazide → 7-Bromo-9-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521625Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C1(O)CCCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[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: 100 °C

Procedure

To a solution of 6-bromo-8-chloro-3,4-dihydroquinoline-2(1H)-thione (80-2; 0.45 g, 0.0016 mol) in cyclohexanol (20 mL) was added acetic hydrazide (0.241 g, 0.0032 mol) and the reaction mixture was heated at 100° C. for 1 h under microwave irradiation conditions. Then 1.5 g of molecular sieves powder was added and the reaction mixture was again heated at 190° C. for 2 h under microwave conditions. The reaction mixture was filtered and the filtrate was evaporated. The crude was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ: 7.85 (s, 1H), 7.76 (s, 1H), 2.87 (bs, 4H), 2.50 (s, 3H). MS (M+1): 298.2.

Workup

additionThen 1.5 g of molecular sieves powder was added
temperaturethe reaction mixture was again heated at 190° C. for 2 h under microwave conditions
filtrationThe reaction mixture was filtered
customthe filtrate was evaporated
customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-807bcec6dab040f4af4d0eed16432e81
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

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