Methanol → 2-(4-Hydroxy-phenyl)-8-methyl-3H-quinazolin-4-one

HRID 1274072Notes

Reaction equation

HRID 1274072 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:14][OH:15]>[Pd]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[N:11]=[C:1]([C:2]1[CH:3]=[CH:4][C:14]([OH:15])=[CH:9][CH:10]=1)[NH:7][C:5]2=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 32713713-Methyl-2-nitrobenzamide

Product 1

HCID 1354713542-(4-Hydroxy-phenyl)-8-methyl-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-Methyl-2-nitrobenzamide (1.20 g, 6.7 mmol) was dissolved in methanol and 10% activated palladium on carbon catalyst (150 mg) was added. The reaction vessel was placed under an atmosphere of hydrogen, at ambient temperature and pressure, until no further hydrogen absorption was observed. The catalyst was removed by filtration of the reaction mixture through a pad of Celite™, which was pre-washed with methanol (150 ml). The solvent was removed under vacuum to give the required product in good yield. The product was used for subsequent reactions without further purification. Yield (0.97 g, 6.4 mmol, 97%), m.p. 145-147° C.

Workup

  1. additionwas added
  2. customwas placed under an atmosphere of hydrogen, at ambient temperature
  3. custompressure, until no further hydrogen absorption
  4. customThe catalyst was removed by filtration of the reaction mixture through a pad of Celite™, which
  5. washwas pre-washed with methanol (150 ml)
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-f70cb71b2d6e4d27b26650ce00641735
Source dataset
uspto-grants-2000_12
Patent number
US06156739

Reaction notes

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