Sodium Acetate → HCID 21252853, compound

HRID 1531012Notes

Reaction equation

HRID 1531012 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:19]3=[C:20]([C:22](=[O:32])[C:23]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:24][N:18]3[C:17]3[CH:16]=[CH:15][C:14]([O:33][CH3:34])=[CH:13][C:12]2=3)[CH:21]=1)C1C=CC=CC=1.C([O-])(=O)C.[Na+].[H][H]>C(O)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:19]3=[C:20]([C:22](=[O:32])[C:23]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:24][N:18]3[C:17]3[CH:16]=[CH:15][C:14]([O:33][CH3:34])=[CH:13][C:12]2=3)[CH:21]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 21252877HCID 21252877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21252853HCID 21252853, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

2-benzyloxy-10-methoxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (470 mg) obtained in Example 252 was dissolved in acetic acid. To the solution were added sodium acetate (259 mg) and palladium carbon (116 mg), and the mixture was heated under reflux in a hydrogen atmosphere for 3 hours. The reaction mixture was filtered, and the filtrate was distilled to remove the solvent under reduced pressure. To the residue was added an aqueous solution of sodium hydrogencarbonate until the termination of foaming. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=20:1) to obtain the title compound (257 mg, 62%).

Workup

  1. temperaturethe mixture was heated
  2. filtrationThe reaction mixture was filtered
  3. distillationthe filtrate was distilled
  4. customto remove the solvent under reduced pressure
  5. additionTo the residue was added an aqueous solution of sodium hydrogencarbonate until the termination of foaming
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=20:1)

Sources & evidence

ORD record
ord-58e8d2b26f634130b1b3971a657e2827
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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