Benzoic acid, 2-amino-5-iodo- → 6-Iodoquinazolin-4-one

HRID 1767145Notes

Reaction equation

HRID 1767145 reaction equation
[I:1][C:2]1[CH:10]=[C:6](C(O)=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.[CH:12]([O-])([O-])OC.[CH3:17][OH:18].[NH3:19]>>[I:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:12][NH:19][C:17]2=[O:18]

Participants

4

Reactant 3

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 21705897Ammonia methanolHCID 53629101Methylorthoformate

Product 1

HCID 1354016666-Iodoquinazolin-4-oneYield 99%

Procedure

In a 2-mL volume stainless steel pressure-resistant vessel were placed 500 mg (1.9 mmol) of 5-iodoanthranilic 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 515 mg (reaction yield: 99%) of 6-iodoquinazolin-4-one.

Workup

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

Sources & evidence

ORD record
ord-c4c5750d09734565a31cc8b65f1771cb
Source dataset
uspto-grants-2007_06
Patent number
US07232903B2

Reaction notes

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