Sodium Acetate → HCID 11172485, compound

HRID 1818900Notes

Reaction equation

HRID 1818900 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:19])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.C([O-])(=O)C.[Na+].[H][H]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][C:4]1[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]2=[CH:2][N:3]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 11471308HCID 11471308, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11172485HCID 11172485, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

8-chloro-6-methyl-5-phenyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (120 mg, 0.438 mmol), palladium acetate (5.0 mg, 0.022 mmol) and sodium acetate (72 mg, 0.877 mmol) were suspended in 5 mL of anhydrous methanol and then stirred at room temperature for about 2 hours under the hydrogen atmosphere. The mixture was filtered and then concentrated under reduced pressure, added with 15 mL of a saturated solution of sodium hydrogen carbonate and then extracted twice with 20 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, filtered and then concentrated. A silica gel column chromatography (2% MeOH/MC) was performed on the resulting residue and 101 mg (96%) of 6-methyl-5-phenyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionadded with 15 mL of a saturated solution of sodium hydrogen carbonate
  4. extractionextracted twice with 20 mL of methylene chloride
  5. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-279ea77ad9b148b48000a2f71120ad08
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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