Boron Trichloride → 4-Chloroquinazolin-8-ol

HRID 1492136Notes

Reaction equation

HRID 1492136 reaction equation
B(Cl)(Cl)Cl.[Cl:5][C:6]1[C:15]2[C:10](=[C:11]([O:16]C)[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1>ClCCl.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:5][C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 2

HCID 25135Boron TrichlorideHCID 102620524-CHLORO-8-METHOXYQUINAZOLINE

Product 1

HCID 157669614-Chloroquinazolin-8-ol

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of boron trichloride in dichloromethane (1.0 molar, 46.0 mL) is added via syringe to a solution of 4-chloro-8-methoxyquinazoline (2.24 g, 11.5 mmol) in chloroform, under a nitrogen atmosphere. The reaction mixture is heated at reflux for 1/2 hour, cooled to room temperature and diluted with a mixture of ice and saturated sodium bicarbonate solution. The phases are separated and the aqueous phase is extracted with chloroform. The organic phases are combined, washed with a 10% ethylenediaminetetraacetic acid (EDTA) solution, dried over MgSO4 and concentrated in vacuo to obtain the title product as a white solid, 1.93 g (93%), mp>252° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 1/2 hour
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with chloroform
  5. washwashed with a 10% ethylenediaminetetraacetic acid (EDTA) solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d9775a14c9c4a32a60a71759846d3d7
Source dataset
uspto-grants-1994_12
Patent number
US05373011

Reaction notes

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