Urea → 2,4-Dihydroxyquinazoline-7-carboxylic acid

HRID 1616122Notes

Reaction equation

HRID 1616122 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15](N)=[O:16]>O>[O:16]=[C:15]1[NH:14][C:4](=[O:6])[C:3]2[C:2](=[CH:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=2)[NH:1]1

Participants

4

Reactant 2

HCID 1176UreaHCID 27248222-Aminoterephthalic acid

Product 1

HCID 196042892,4-Dihydroxyquinazoline-7-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Into a round bottom flask was added 2-aminoterephthalic acid (0.83 g, 4.6 mmol) and urea (2.75 g, 45.8 mmol). The reaction mixture was heated to 160° C. and stirred overnight. The mixture was cooled to rt, water added and the solid was filtered. The solid was then washed with acetic acid to afford 2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid (0.87 g, 92%). LC-MS: (FA) ES+ 207.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationthe solid was filtered
  3. washThe solid was then washed with acetic acid

Sources & evidence

ORD record
ord-98a84cca8c8c481cb09e50c3327bab43
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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