Formamide → 6,7-Dimethoxy-3H-quinazolin-4-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[CH:10][C:11]=1[O:12][CH3:13])[C:7](O)=[O:8].[CH:15]([NH2:17])=O>O>[CH3:13][O:12][C:11]1[CH:10]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:14]=[CH:15][NH:17][C:7]2=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 190 °C
Procedure
A mixture of 4,5-dimethoxyanthranilic acid (19.7 g, 100 mmol) and formamide (10 ml) was heated at 190° C. for 5 hours. The mixture was allowed to cool to approximately 80° C. and water (50 ml) was added. The mixture was then allowed to stand at ambient temperature for 3 hours. Collection of the solid by suction filtration, followed by washing with water (2×50 ml) and drying in vacuo, yielded 6,7-dimethoxy-3,4-dihydroquinazolin-4-one (3.65 g, 18% yield) as a white solid:
Workup
- temperatureto cool to approximately 80° C.
- customCollection of the solid
- filtrationby suction filtration
- washby washing with water (2×50 ml)
- customdrying in vacuo
Sources & evidence
- ORD record
- ord-9e0a056d746245b7bfae2459b3ab324e
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07235559B1
Reaction notes
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