Dimethylformamide → HCID 9795416, compound

HRID 1249757Notes

Reaction equation

HRID 1249757 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

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15816962HCID 15816962, compound

Product 1

HCID 9795416HCID 9795416, compound

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

  1. distillationThe DMF is then distilled off under reduced pressure
  2. washThe crude product is washed successively with ethyl acetate, methanol
  3. customAfter drying

Sources & evidence

ORD record
ord-624b042d7cc948eebccd83d54b449b2c
Source dataset
uspto-grants-2002_01
Patent number
US06335346B1

Reaction notes

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