Sodium Hydroxide → 2-(2-chloro-6-methoxy-phenyl)-3H-quinazolin-4-one

HRID 2079306

Reaction equation

HRID 2079306 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=O)[C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:20])(=[O:3])[NH2:2].[OH-].[Na+]>C(O)(=O)C>[Cl:20][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:12]=1[C:11]1[NH:2][C:1](=[O:3])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58010809N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide

Product 1

HCID 1361216082-(2-chloro-6-methoxy-phenyl)-3H-quinazolin-4-oneYield 14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide (13 g, 42.7 mmol) was suspended in 100 mL of a 2 N NaOH solution and heated to reflux. After refluxing for 3 hours, another 25 mL of a 2 N NaOH solution was added, and the reaction was refluxed for another hour. The mixture was cooled to room temperature and acidified with acetic acid to pH 5. The formed precipitate was collected by filtration. The product was purified over alumina using EtOAc as an eluent giving 1.7 g (5.9 mmol, 14%) of 2-(2-chloro-6-methoxy-phenyl)-3H-quinazolin-4-one.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for 3 hours
  3. temperaturethe reaction was refluxed for another hour
  4. filtrationThe formed precipitate was collected by filtration
  5. customThe product was purified over alumina

Sources & evidence

ORD record
ord-63d7c787c42241aaa8a812e5bd29591e
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Linked notes

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