Ethanol → 2-(2-Ethoxyphenyl)-8-methylquinazolin-4(3H)-one
Reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][C:9]1[C:17](OC)=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])=O)[CH3:2].[C:24](=O)([O-])[O-].[K+].[K+].OO.C(O)C>ClCCl.O>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]1[NH:13][C:11](=[O:12])[C:10]2[C:9](=[C:17]([CH3:24])[CH:16]=[CH:15][CH:14]=2)[N:8]=1)[CH3:2]Participants
Procedure
A stirred mixture of 2-(2-ethoxybenzamido)-3-methoxybenzamide (2.6 g, 0.0083 mol), anhydrous potassium carbonate (2.33 g, 0.017 mol), hydrogen peroxide (30%, 4 ml), ethanol (40 ml) and water (80 ml) was heated under reflux for 1 hour. The mixture was allowed to cool and poured into a mixture of water (200 ml) and dichloromethane (100 ml), then the aqueous phase separated, acidified to pH 4 by the addition of 2N hydrochloric acid and extracted with dichloromethane (2×100 ml). The organic solutions were combined, dried (MgSO4) and evaporated under vacuum to give the title compound, which crystallized from ethyl acetate as a colorless solid (2.8 g, 83%), m.p. 198°-199° C. Found: C,68.88; H,5.50; N,9.30. C17H16N2O3 requires C,68.91; H,5.44; N,9.45%.
Workup
- temperaturewas heated
- temperatureunder reflux for 1 hour
- temperatureto cool
- customthe aqueous phase separated
- additionacidified to pH 4 by the addition of 2N hydrochloric acid
- extractionextracted with dichloromethane (2×100 ml)
- dry with materialdried (MgSO4)
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-18625a4fd17944b194bae4d20b208430
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05482941
Reaction notes
Loading…