Methanol → 6,7-Dimethoxy-3H-quinazolin-4-one
Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4](O)=[O:5].COC(OC)OC.C([O-])=O.[NH4+:25].[CH3:26]O>O>[CH3:14][O:13][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH3:12])[N:1]=[CH:26][NH:25][C:4]2=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A suspension of 2-amino-4,5-dimethoxybenzoic acid (23.40 g), trimethoxymethane (52 mL), ammonium formate (30.00 g) and methanol (400 mL) was heated to 70° C. and refluxed for 4 h. After the reaction mixture was cooled to room temperature, 160 mL of water was added to the reaction. The mixture was filtered to afford the title compound as a yellow solid (22.70 g, 93.00%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, d6-DMSO) δ: 3.87 (s, 3H), 3.91 (s, 3H), 7.13 (s, 1H), 7.45 (s, 1H), 7.98 (s, 1H).
Workup
- temperaturerefluxed for 4 h
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationThe mixture was filtered
Sources & evidence
- ORD record
- ord-45f80623c03f4f24846c106a70b5c2d2
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181277B2
Reaction notes
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