Acetic Acid → 2-Chloroquinazolin-4(3H)-one

HRID 1295729Notes

Reaction equation

HRID 1295729 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([Cl:12])[N:3]=1.[OH-].[K+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=[O:35])C>C1COCC1>[Cl:12][C:4]1[NH:3][C:2](=[O:35])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 2528862,4-DichloroquinazolineHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 1354432322-Chloroquinazolin-4(3H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3 g (11 mmol) of the dichloroquinazoline (1A) in 50 mL THF was stirred with 30 mL of 40% aqueous KOH and 3 mL of 40% aqueous tetrabutylammonium hydroxide for 3 days. The layers were allowed to separate and the upper layer was concentrated to give a white solid. This was treated with dilute acetic acid and the solid was collected and washed with water, then dried at 65° C. in vacuo to afford 2.4 g (86%) of the 2-chloroquinazolin-4-one (1). Mp 251–251.7° C.; MS (ES+) m/z 255 (M+H)+. Anal. (C11H11ClN2O3) Calcd.: C, 51.88; H, 4.35; N, 11.00. Found: C, 51.94; H, 4.34; N, 10.95.

Workup

  1. customto separate
  2. concentrationthe upper layer was concentrated
  3. customto give a white solid
  4. customthe solid was collected
  5. washwashed with water
  6. customdried at 65° C. in vacuo

Sources & evidence

ORD record
ord-c266d33188c7413aa7d1a970cca26bc5
Source dataset
uspto-grants-2007_07
Patent number
US07244738B2

Reaction notes

Loading…