Acetic Acid → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 1357690Notes

Reaction equation

HRID 1357690 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH3:20])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:21]N(C=NC=[N+](C)C)C.[Cl-].C([O-])(=O)C.[Na+].C(O)(=O)C>O1CCOCC1>[CH2:12]([O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][CH:21]=[N:1]2)=[CH:7][C:8]=1[O:19][CH3:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 11008255Gold's ReagentHCID 124714802-Amino-4-(benzyloxy)-5-methoxybenzamide

Product 1

HCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-oneYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem. 1977, vol 20, 146-149, 10 g) and Gold's reagent (7.4 g) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g) and acetic acid (1.65 ml) were added to the reaction mixture and it was heated for a further 3 hours. The mixture was evaporated to dryness, water was added to the residue and the solid was filtered off, washed with water and dried. Recrystallization from acetic acid gave 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (8.7 g, 84%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperaturewas heated for a further 3 hours
  4. customThe mixture was evaporated to dryness, water
  5. additionwas added to the residue
  6. filtrationthe solid was filtered off
  7. washwashed with water
  8. customdried
  9. customRecrystallization from acetic acid

Sources & evidence

ORD record
ord-661e8571f79642a4ad30913188935f6f
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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