Dimethylformamide → HCID 9839231, compound

HRID 1249758Notes

Reaction equation

HRID 1249758 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:23])[CH2:20][CH2:21][CH3:22].CN(C=[O:28])C>>[C:19]([N:5]1[CH2:6][C:7]2[C:8](=[O:28])[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:23])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 18328989HCID 18328989, compound

Product 1

HCID 9839231HCID 9839231, compoundYield 40%

Procedure

NaH (1.5 eq; 60% suspension in oil) is added to a solution of 1-methylene-2-butyryl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (160 mg; 0.6 mmol) in DMF (3 ml). The mixture is stirred under an oxygen atmosphere for 6 hours. The DMF is then distilled off under reduced pressure. The crude product is washed several times with ethyl acetate. After filtration and drying, 2-butyryl-7-methoxy-3-methylene-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=40%).

Workup

  1. distillationThe DMF is then distilled off under reduced pressure
  2. washThe crude product is washed several times with ethyl acetate
  3. filtrationAfter filtration
  4. customdrying

Sources & evidence

ORD record
ord-b4feaa720b274a859021ceb65d824140
Source dataset
uspto-grants-2002_01
Patent number
US06335346B1

Reaction notes

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