HCID 23369598, compound → HCID 10976036, compound

HRID 1900830Notes

Reaction equation

HRID 1900830 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[H][H]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2

Participants

5

Reactant 2

HCID 23369598HCID 23369598, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10976036HCID 10976036, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5-Hydroxy-8-methylcarbostyril (20.0 g, 0.114M) was dissolved in acetic acid (800 ml). To the solution, 10% palladium-on-carbon (10.0 g) was added. The mixture was stirred at 80° C. for 4 hours in the stream of hydrogen. The reaction mixture was filtered, and the filtrate was distilled off under reduced pressure. The residue was extracted from a mixture of chloroform-methanol (10:1) and saturated aqueous sodium bicarbonate solution. The organic phase was washed with saturated aqueous NaCl solution, dried, and condensed under reduced pressure. The resultant residue was recrystallized from methanol-ether to obtain 20.2 g of the title compound as pale yellow powdery crystals (99.9%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was distilled off under reduced pressure
  3. extractionThe residue was extracted from a mixture of chloroform-methanol (10:1) and saturated aqueous sodium bicarbonate solution
  4. washThe organic phase was washed with saturated aqueous NaCl solution
  5. customdried
  6. customcondensed under reduced pressure
  7. customThe resultant residue was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-a6026dee68434b418560ec6abe514522
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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