2-Amino-4-chlorobenzoic acid → 7-Chloro-3H-quinazolin-4-one

HRID 1767144Notes

Reaction equation

HRID 1767144 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)C(O)=O.[CH:12]([O-])([O-])OC.[CH3:17][OH:18].[NH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:17](=[O:18])[NH:19][CH:12]=[N:11]2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 666462-Amino-4-chlorobenzoic acidHCID 21705897Ammonia methanolHCID 53629101Methylorthoformate

Product 1

HCID 1354161757-Chloro-3H-quinazolin-4-oneYield 99%

Procedure

In a 2-mL volume stainless steel pressure-resistant vessel were placed 330 mg (1.9 mmol) of 4-chloroanthranilic acid, 403 mg (3.8 mmol) of methyl orthoformate, and 1.2 mL (8.4 mmol) of 15 wt. % ammonia methanol solution. The reaction was carried out at 120° C. for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and analyzed (according to absolute quantitative analysis) by high performance liquid chromatography. There was produced 343 mg (reaction yield: 99%) of 7-chloroquinazolin-4-one.

Workup

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

Sources & evidence

ORD record
ord-e7903440e9bf485cb03d196a4f6cfdb7
Source dataset
uspto-grants-2007_06
Patent number
US07232903B2

Reaction notes

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