2-Amino-6-chlorobenzoic acid → 5-Chloroquinazolin-4(1H)-one

HRID 2296709Notes

Reaction equation

HRID 2296709 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8](O)=[O:9].[N:12]1[CH:17]=CC=NN=1>CCO.N1CCCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:9])[NH:12][CH:17]=[N:11]2

Participants

5

Reactant 2

HCID 750712-Amino-6-chlorobenzoic acidHCID 1230471,2,3-Triazine

Product 1

HCID 1354299165-Chloroquinazolin-4(1H)-oneYield 70%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-chloro anthranilic acid (2.12 g, 12.3 mmol) and triazine (1.0 g, 12.3 mmol) in EtOH (40 mL) containing piperidine (3 drops) was heated under reflux with stirring for 8 h. On cooling crystals formed, which were filtered to yield 5-chloroquinazolin-4-one (1.55 g, 70%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureOn cooling crystals
  4. customformed
  5. filtrationwhich were filtered

Sources & evidence

ORD record
ord-44ca4e1dec1f4e379aafc5828e0fef39
Source dataset
uspto-grants-2002_12
Patent number
US06489328B2

Reaction notes

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