2,4-Dichloroquinazoline → 2-Chloroquinazoline

HRID 1276595Notes

Reaction equation

HRID 1276595 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>C(Cl)Cl.[Cl-].[Na+].O.[Zn]>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 1

HCID 2528862,4-Dichloroquinazoline

Product 1

HCID 740542-Chloroquinazoline

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2,4-dichloroquinazoline (5 g) in methylene chloride (100 mL) is combined with 100 mL of saturated brine containing 9% NH4OH and powdered zinc (5 g). The resultant mixture is refluxed for 4 hours, cooled and filtered through celite. The organic layer is removed, diluted with ethyl acetate (100 ml), washed with 1 N HCl solution, dried and concentrated to yield 2-chloro-quinazoline.

Workup

  1. temperaturecooled
  2. filtrationfiltered through celite
  3. customThe organic layer is removed
  4. additiondiluted with ethyl acetate (100 ml)
  5. washwashed with 1 N HCl solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c6935bf324a418aa5884e6efb8edf05
Source dataset
uspto-grants-2000_12
Patent number
US06166205

Reaction notes

Loading…