Sodium hydride → HCID 22414273, compound

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O-:15].[Na+].[H-].[Na+]>CO>[Cl:13][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH3:12])=[CH:11][C:2]([O:15][CH3:14])=[N:3]2)=[CH:8][CH:7]=1

Participants

Procedure

2-Chloroquinoline 14 (7.0 g; 32.8 mmol) was added to a solution of sodium methoxide in methanol generated from 1.08 g (36.1 mmol) of 80% sodium hydride in 80 ml of methanol. The resulting mixture was refluxed overnight. It was filtered while still hot to remove undissolved matter. The product crystallized from the methanol upon cooling to deliver 6.1 g (70%) of 15 as a white solid. 1H NMR (CDCl3): δ 2.62 (s, 3H); 4.10 (s, 3H); 6.78 (s, 1H); 7.38 (d, 1H); 7.81 (d, 1H); 7.93 (d, 1H).