Hydrochloric Acid → 4-Oxo-3,4-dihydroquinazoline-6-carboxylic acid

HRID 384759

Reaction equation

HRID 384759 reaction equation
[C:1]([C:4]1[CH:12]=[C:8]([C:9](O)=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH:14]([O-])([O-])OC.C([O-])(=O)C.[NH4+:23].Cl>O.CO>[C:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:13]=[CH:14][NH:23][C:9]2=[O:10])([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 113558524-Aminobenzene-1,3-dioic acidHCID 53629101Methylorthoformate

Product 1

HCID 1357038814-Oxo-3,4-dihydroquinazoline-6-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.00 g (5.5 mmol) of 5-carboxyanthranilic acid, 2.30 g (22.0 mmol) of methyl orthoformate, 1.70 g (22.0 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 and 10 mL of hydrochloric acid (1 mol/L) were added to the reaction mixture. The resulting aqueous mixture was stirred for 15 minutes and filtered to give 0.96 g (isolated yield: 84%, purity: 91% in terms of area percentage determined by high performance liquid chromatography) of 6-carboxyquinazolin-4-one as a yellow crystalline product.

Workup

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

Sources & evidence

ORD record
ord-0254755dddaa433fb2751a3513550e4f
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Linked notes

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