tert-Butoxy bis(dimethylamino)methane → [2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamine
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.C(O[CH:20](N(C)C)[N:21]([CH3:23])[CH3:22])(C)(C)C>>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]=[CH:20][N:21]([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1Participants
3
Conditions
- Temperature
- 120 °C
Procedure
2-Chloro-6-methoxy-4-methylquinoline (25 g, 0.12 mol) and tert-butoxybis(dimethylamino)methane (Bredereck's reagent) (30 g, 0.17 mol) was stirred under heating at 120° C. for 1.5 hours. After cooling the reaction mixture, the precipitated crystals were washed with diisopropyl ether to obtain the title compound (29.2 g, 92%).