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

HRID 1668678Notes

Reaction equation

HRID 1668678 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 (10 g, 40 mmol), (J. Med. Chem. 1977, vol 20, 146-149), and Gold's reagent (7.4 g, 50 mmol) in dioxane (100 mL) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 37 mmol) and acetic acid (1.65 mL, 29 mmol) were added to the reaction mixture and it was heated for a further 3 hours. The volatiles were removed by evaporation, water was added to the residue, the solid was collected by filtration, washed with water and dried. Recrystallisation 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 volatiles were removed by evaporation, water
  5. additionwas added to the residue
  6. filtrationthe solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customRecrystallisation from acetic acid

Sources & evidence

ORD record
ord-cea78948c0ee46dcaacf2a816d0fbbda
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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