Acetic Anhydride → 7-Acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one

HRID 1668671Notes

Reaction equation

HRID 1668671 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14].[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1356099526-Methoxy-7-hydroxyquinazolin-4-one

Product 1

HCID 1356979057-Acetoxy-6-methoxy-3,4-dihydroquinazolin-4-oneYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

Pyridine (20 ml) was added to a suspension of 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one (20.5 g, 107 mmol) in acetic anhydride (150 ml, 1.6 mol). The reaction mixture was heated to 120° C. for three hours, during which time the solid dissolved. The reaction mixture was allowed to cool then poured into ice-water (900 ml). The reaction mixture was stirred for one hour then the solid was removed by filtration and dried over phosphorus pentoxide yielding 7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one as a white solid (20.98 g, 84%).

Workup

  1. dissolutiondissolved
  2. temperatureto cool
  3. customthe solid was removed by filtration
  4. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-b9fa3e15748545268f8da333005f8ba3
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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