Methanol → 4(1H)-Quinazolinone

HRID 384760Notes

Reaction equation

HRID 384760 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:21].[CH3:22]O>>[N:4]1[C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1](=[O:10])[NH:21][CH:22]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8635Methyl AnthranilateHCID 517165Ammonium AcetateHCID 53629101Methylorthoformate

Product 1

HCID 1354087534(1H)-QuinazolinoneYield 98%

Procedure

In a 2-mL volume stainless steel pressure-resistant vessel were placed 302 mg (2.0 mmol) of methyl anthranilate, 424 mg (4.0 mmol) of methyl orthoformate, 308 mg (4.0 mmol) of ammonium acetate, and 1.0 mL of methanol. The reaction was carried out at 120° C. for 3 hours. After the reaction was complete, the reaction mixture was analyzed (according to absolute quantitative analysis) by high performance liquid chromatography. There was produced 285 mg (reaction yield: 98%) of quinazolin-4-one.

Workup

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

Sources & evidence

ORD record
ord-438196201add4b2d9acf38d98ab5f91c
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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