Methyl formate → 6-Iodoquinazolin-4-one

HRID 1767147Notes

Reaction equation

HRID 1767147 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](OC)=O.[CH3:16][OH:17].[NH3:18]>>[I:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:12][NH:18][C:16]2=[O:17]

Participants

4

Reactant 3

HCID 7865Methyl formateHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 21705897Ammonia methanol

Product 1

HCID 1354016666-Iodoquinazolin-4-oneYield 77%

Procedure

In a 2-mL volume stainless steel pressure-resistant vessel were placed 500 mg (1.9 mmol) of 5-iodoanthranilic acid, 342 mg (5.7 mmol) of methyl formate, and 1.2 mL (8.4 mmol) of 15 wt. % ammonia methanol solution. The reaction was carried out at 150° C. for 4 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 401 mg (reaction yield: 77%) of 6-iodoquinazolin-4-one.

Workup

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

Sources & evidence

ORD record
ord-37c878bfc7f74ec6b1d4b6d87229e3e8
Source dataset
uspto-grants-2007_06
Patent number
US07232903B2

Reaction notes

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