Dimethylformamide → HCID 9795416, compound
Reaction equation
[H-].[Na+].[CH2:3]=[C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][N:5]1[C:19](=[O:21])[CH3:20].CN(C=[O:26])C>>[C:19]([N:5]1[CH2:6][C:7]2[C:8](=[O:26])[C:9]3[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=3[NH:15][C:16]=2[C:4]1=[CH2:3])(=[O:21])[CH3:20]Participants
4
Procedure
NaH (1.5 eq; 60% suspension in oil) is added to a solution of 1-methylene-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (1 g; 3.9 mmol) in DMF (5 ml). The mixture is stirred under an oxygen atmosphere overnight. The DMF is then distilled off under reduced pressure. The crude product is washed successively with ethyl acetate, methanol and then ether. After drying, 2-acetyl-7-methoxy-3-methylene-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained.
Workup
- distillationThe DMF is then distilled off under reduced pressure