Formamide → 4-Oxo-3,4-dihydroquinazoline-6-carboxylic acid

HRID 1094731Notes

Reaction equation

HRID 1094731 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=O.[CH:14]([NH2:16])=O>CC(C)=O>[O:13]=[C:11]1[C:3]2[C:2](=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[N:1]=[CH:14][NH:16]1

Participants

4

Reactant 2

HCID 713FormamideHCID 113558524-Aminobenzene-1,3-dioic acid

Product 1

HCID 1357038814-Oxo-3,4-dihydroquinazoline-6-carboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-amino isophthalic acid (2 g, 11.04 mmol) and formamide (10 mL) was heated at 180° C. for 5 h. The reaction mixture was cooled to RT and acetone was added. The solid precipitate thus obtained was stirred for 2 h, filtered and dried to give 4-oxo-3,4-dihydroquinazoline-6-carboxylic acid in 50% yield.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customThe solid precipitate thus obtained
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-6cca4686921a40558941bd2d62410f14
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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