Methanol → 6,7-Dimethoxy-3H-quinazolin-4-one

HRID 384756Notes

Reaction equation

HRID 384756 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].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:24].[CH3:25]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:25][NH:24][C:7]2=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 797364,5-Dimethoxyanthranilic acidHCID 517165Ammonium AcetateHCID 53629101Methylorthoformate

Product 1

HCID 1354950166,7-Dimethoxy-3H-quinazolin-4-oneYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.00 g (5.1 mmol) of 4,5-dimethoxyanthranilic acid, 2.15 g (20.3 mmol) of methyl orthoformate, 1.56 g (20.3 mmol) of ammonium acetate, and 4.0 mL of methanol. The reaction was carried out at 120° C. for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and 40 mL of water was added to the reaction mixture. The resulting aqueous mixture was stirred for 15 minutes and filtered to give 0.96 g (isolated yield: 92%) of 6,7-dimethoxyquinazolin-4-one as a brown crystalline product.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-fb2601d43b60452a9f47e1bc7ded1031
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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