Methanol → 6-Iodoquinazolin-4-one

HRID 384754

Reaction equation

HRID 384754 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.C([O-])([O-])OC.C([O-])(=O)C.[NH4+:21].[CH3:22]O>O>[I:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[CH:22][NH:21][C:7]2=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 517165Ammonium AcetateHCID 53629101Methylorthoformate

Product 1

HCID 1354016666-Iodoquinazolin-4-oneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.0 g (3.8 mmol) of 5-iodoanthranilic acid, 0.81 g (7.6 mmol) of methyl orthoformate, 0.59 g (7.6 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 0.97 g (isolated yield: 93%) of 6-iodoquinazolin-4-one as a pale gray crystalline product.

Workup

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

Sources & evidence

ORD record
ord-e0cee7944b3d4854b339820c84655ba9
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Linked notes

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