Acetohydrazide → 7-Bromo-9-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline
Reaktionsgleichung
[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]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
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.