Dimethylformamide → HCID 9796204, compound

HRID 1249759Notes

Reaction equation

HRID 1249759 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]([CH:21]1[CH2:23][CH2:22]1)=[O:20].CN(C=[O:28])C>>[CH:21]1([C:19]([N:5]2[CH2:6][C:7]3[C:8](=[O:28])[C:9]4[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=4[NH:15][C:16]=3[C:4]2=[CH2:3])=[O:20])[CH2:22][CH2:23]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 18328985HCID 18328985, compound

Product 1

HCID 9796204HCID 9796204, compoundYield 38%

Procedure

NaH (1.2 eq; 60% suspension in oil) is added to a solution of 1-methylene-2-cyclopropylcarbonyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (500 mg; 1.7 mmol) in DMF (5 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 off. 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/CH2Cl2 mixture (10/90), acetone and then ethyl acetate. After drying, 2-cyclopropylcarbonyl-7-methoxy-3-methylene-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=38%).

Workup

  1. stirringstirring
  2. waitis continued overnight
  3. distillationThe DMF is then distilled off under reduced pressure
  4. filtrationfiltered off
  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-ca1a6e87b0454b988d4c8e0e69a5076b
Source dataset
uspto-grants-2002_01
Patent number
US06335346B1

Reaction notes

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