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

HRID 1668669Notes

Reaction equation

HRID 1668669 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, 0.04 mol), (J. Med. Chem. 1977, vol 20, 146-149), and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the reaction mixture and it was heated for a further 3 hours. The mixture was evaporated, water was added to the residue, the solid was filtered off, washed with water and dried (MgSO4). 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 mixture was evaporated
  5. additionwater was added to the residue
  6. filtrationthe solid was filtered off
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. customRecrystallisation from acetic acid

Sources & evidence

ORD record
ord-4aa85b3121bf436a97ab78986107cd5b
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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