Acetic Acid → 2-Chloro-6-methyl-3,4-dihydroquinazolin-4-one

HRID 540217Notes

Reaction equation

HRID 540217 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[OH-].[Na+].C(O)(=[O:18])C>O1CCCC1>[Cl:1][C:2]1[NH:11][C:10](=[O:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 142564832,4-Dichloro-6-methylquinazoline

Product 1

HCID 1355887902-Chloro-6-methyl-3,4-dihydroquinazolin-4-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-6-methylquinazoline (2.13 g, 10 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (2 N, 20 mL). After being stirred at room temperature for 4 hours, the reaction mixture was chilled and acidified to pH 5 with acetic acid. The formed solid was collected by filtration, washed with water, and dried in vacuo to afford 1.7 g of the desired product as a white solid (yield was 87.6%).

Workup

  1. temperaturethe reaction mixture was chilled
  2. filtrationThe formed solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d07f5c55160a487eba117c1271a7bfe4
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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