Sodium Hydroxide → 7-Bromo-3,4-dihydroquinazolin-4-one

HRID 968572Notes

Reaction equation

HRID 968572 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([O-])(=O)C.[Na+].[OH-:16].[Na+]>C(O)=O>[Br:10][C:8]1[CH:9]=[C:2]2[C:3]([C:4](=[O:16])[NH:5][CH:11]=[N:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 99206362-Amino-4-bromobenzonitrile

Product 1

HCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 2-amino-4-bromo-benzonitrile (550 mg, 2.79 mmol) in formic acid, add sodium acetate (435 mg, 5.30 mmol) in one portion. Reflux the reaction mixture for 16 h then remove the formic acid under reduced pressure to give a solid. Add 20% aqueous NaOH and stir for 1 hour. Remove the undissolved solids via filtration and acidify the filtrate with 12N HCl to produce a white solid. Collect the solid via filtration and wash it with water (5×) and ether (1×) to give 7-bromo-3H-quinazolin-4-one as an off-white solid.

Workup

  1. temperatureReflux the reaction mixture for 16 h
  2. customthen remove the formic acid under reduced pressure
  3. customto give a solid
  4. customRemove the undissolved solids
  5. filtrationvia filtration
  6. customto produce a white solid
  7. customCollect the solid
  8. filtrationvia filtration
  9. washwash it with water (5×) and ether (1×)

Sources & evidence

ORD record
ord-4e0dfcbb6d004318b0169ee949a09325
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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