Dimethylformamide → 2-Acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline

HRID 1249760Notes

Reaction equation

HRID 1249760 reaction equation
[H-].[Na+].[CH3:3][CH: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[CH:4]1[CH3:3])(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 18328986HCID 18328986, compound

Product 1

HCID 98383642-Acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinolineYield 45%

Procedure

NaH (1.2 eq; 60% suspension in oil) is added to a solution of 1-methyl-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (1.56 g; 6.0 mmol) in DMF (20 ml). The mixture is stirred under an oxygen atmosphere for 48 hours, further NaH (1.1 eq) is then added and stirring is continued overnight. The DMF is then distilled off under reduced pressure. The crude product is taken up in water and then filtered. Saturated NH4Cl solution is added to the aqueous phase. The mixture is stirred for 30 minutes. The precipitate is filtered off and then washed successively with water, an MeOH/CH2Cl mixture (10/90), acetone and then ethyl acetate. After drying, 2-acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=45%).

Workup

  1. stirringstirring
  2. waitis continued overnight
  3. distillationThe DMF is then distilled off under reduced pressure
  4. filtrationfiltered
  5. additionSaturated NH4Cl solution is added to the aqueous phase
  6. stirringThe mixture is stirred for 30 minutes
  7. filtrationThe precipitate is filtered off
  8. washwashed successively with water
  9. customAfter drying

Sources & evidence

ORD record
ord-e68ba8361a354520bc0875d882399971
Source dataset
uspto-grants-2002_01
Patent number
US06335346B1

Reaction notes

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