Hydrochloric Acid → 2-(2-methoxyphenyl)-3H-quinazolin-4-one

HRID 2079233Notes

Reaction equation

HRID 2079233 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.[C:18](Cl)(=O)[C:19]1[C:20]([O:25][CH3:26])=[CH:21][CH:22]=[CH:23][CH:24]=1.Cl>C1COCC1>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[NH:10][C:1](=[O:9])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 8471TriethylamineHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 1354360052-(2-methoxyphenyl)-3H-quinazolin-4-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a cooled (0-5° C.) mixture of anthranilamide (350 g, 2.57 mol) and triethylamine (286 g, 2.83 mol) in THF (2.5 L) was added dropwise o-anisoyl chloride (437 g, 2.57 mol) while maintaining the temperature between 0-20° C. The resulting suspension was stirred at room temperature overnight. The solvent was evaporated in vacuo, and the residue was washed several times with water. The wet residue was suspended in 2 M aq. NaOH (13 L), and the mixture was heated to reflux. After 20 minutes a clear solution was obtained. After 1 h of reflux the clear solution was cooled in an ice water bath and then acidified to pH 6 with conc. aq. HCl. The suspension was filtered, and the residue was washed thoroughly with water. The white solid was dried by azeotropic distillation with toluene. 2-(2-Methoxyphenyl)quinazolin-4(3H)-one (567 g) was obtained in 82%. 1H-NMR (200 MHz, Me2SO-d6): δ 3.90 (s, 3 H), 7.20 (m, 2 H), 7.60 (t, 2 H), 7.85 (m, 3 H), 8.20 (d, 1 H), 12.20 (s, 1 H).

Workup

  1. temperatureTo a cooled
  2. customThe solvent was evaporated in vacuo
  3. washthe residue was washed several times with water
  4. temperaturethe mixture was heated to reflux
  5. customAfter 20 minutes a clear solution was obtained
  6. temperatureAfter 1 h of reflux the clear solution
  7. temperaturewas cooled in an ice water bath
  8. filtrationThe suspension was filtered
  9. washthe residue was washed thoroughly with water
  10. dry with materialThe white solid was dried by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-61068e9d87204441b79e8cbd8420e528
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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