Acetic Acid → HCID 135984388, compound

HRID 1596280Notes

Reaction equation

HRID 1596280 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:26])[NH:14][C:15]([C:19](=[O:25])[C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(=O)C>[Pd].C(OCC)(=O)C.CO.CN(C=O)C>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:26])[NH:14][C:15]([C:19](=[O:25])[C:20]([CH3:23])([CH3:24])[CH2:21][CH3:22])=[N:16]2)=[CH:11][CH:10]=1

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 1361618157-Benzyloxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 135984388HCID 135984388, compoundYield 83.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5% Palladium-on-charcoal catalyst (0.7 g, 50% in water) was added to a solution of 7-benzyloxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one (6.85 g, 18.7 mmol) in ethyl acetate (300 ml), methanol (40 ml), DMF (40 ml), and acetic acid (0.7 ml). The mixture was vigorously stirred under hydrogen at atmospheric pressure for 4.5 hours. The catalyst was removed by filtration through diatomaceous earth, the filtrate concentrated by evaporation to about 60 ml, diluted with water (300 ml) and extracted with ether (3×300 ml). The combined extracts were washed with brine, dried (MgSO4), and the volatiles removed by evaporation. The resulting crude solid was dissolved in acetone (200 ml) and acetic acid (0.2 ml) and cooled to 0° C. Potassium permanganate (1.8 g) was added and the mixture stirred for 10 minutes. The reaction mixture was poured into water (250 ml) and ethyl acetate (250 ml) was added. The precipitate was removed ;by filtration, the organic phase separated and the aqueous phase re-extracted with ethyl acetate (2×100 ml). The combined extracts were washed with water and brine, dried (MgSO4) and the volatiles removed by evaporation to give 7-hydroxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one (4.05 g, 78%) as a cream solid.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated by evaporation to about 60 ml
  3. additiondiluted with water (300 ml)
  4. extractionextracted with ether (3×300 ml)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe volatiles removed by evaporation
  8. dissolutionThe resulting crude solid was dissolved in acetone (200 ml)
  9. additionPotassium permanganate (1.8 g) was added
  10. stirringthe mixture stirred for 10 minutes
  11. additionThe reaction mixture was poured into water (250 ml) and ethyl acetate (250 ml)
  12. additionwas added
  13. customThe precipitate was removed ;by filtration
  14. customthe organic phase separated
  15. extractionthe aqueous phase re-extracted with ethyl acetate (2×100 ml)
  16. washThe combined extracts were washed with water and brine
  17. dry with materialdried (MgSO4)
  18. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-de7aca05ab9f4fbeb93efe7f968d3e0d
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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