HCID 722983, compound → 2-(3-pyridyl)quinazolin-4-one

HRID 1648214Notes

Reaction equation

HRID 1648214 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH2:14])=[O:13])=O)[CH:2]=1.C[O-].[Na+]>C1(C)C=CC=CC=1.[Cl-].[NH4+]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:14][C:12](=[O:13])[C:11]3[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:9]=2)[CH:2]=1

Participants

5

Reactant 2

HCID 722983HCID 722983, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 1354122732-(3-pyridyl)quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of the benzamide compound (11.5 g, prepared in Reference example 6) in 100 mL of toluene was added 95% sodium methoxide (5.7 g). The solution was heated at 60°-80° C. for three hours under nitrogen atmosphere. After cooling to room temperature, the solution was diluted with ammonium chloride solution. After stirring for one-half hour, the mixture was filtered. An NMR of the filtered material indicated the reaction was incomplete. The material was taken up in toluene and ethanol and 95% sodium methoxide (5.7 g) was added. The resulting solution was heated to reflux and stirred via a mechanical stirrer, under nitrogen atmosphere, overnight. The solvent had evaporated and the concentrate in the flask was collected and washed with ammonium chloride solution and methylene chloride. The solid material was collected by filtration and allowed to dry to give the title compound as a gray powder having the following physical data.

Workup

  1. temperatureThe solution was heated at 60°-80° C. for three hours under nitrogen atmosphere
  2. filtrationthe mixture was filtered
  3. additionethanol and 95% sodium methoxide (5.7 g) was added
  4. temperatureThe resulting solution was heated
  5. temperatureto reflux
  6. stirringstirred via a mechanical stirrer, under nitrogen atmosphere, overnight
  7. customThe solvent had evaporated
  8. concentrationthe concentrate in the flask
  9. customwas collected
  10. washwashed with ammonium chloride solution and methylene chloride
  11. filtrationThe solid material was collected by filtration
  12. customto dry

Sources & evidence

ORD record
ord-24ef03fcfd864c9589c41d0c2b3857c0
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Reaction notes

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