Sodium Hydroxide → 4-Chloro-6-methoxyquinazoline

HRID 1013726Notes

Reaction equation

HRID 1013726 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=O.O=P(Cl)(Cl)[Cl:16].[OH-].[Na+]>>[Cl:16][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1354514236-Methoxyquinazolin-4-OL

Product 1

HCID 111831744-Chloro-6-methoxyquinazoline

Conditions

Temperature
105 °C

Procedure

A pressure resistant bottle was charged with 6-methoxyquinazolin-4(3H)-one (1.0 g, 5.68 mmol) and POCl3(17.5 ml, 187.3 mmol). The resulting mixture was heated at 105° C. for 18 hours. The reaction mixture was cooled to RT and poured onto ice slurry while stirring heavily. The solution was quickly neutralized with 6N NaOH, and product extracted with DCM. The organic layer was collected, dried over sodium sulfate and concentrated to afford 4-chloro-6-methoxyquinazoline as tan solid. MS: [M+H]=194.9; Calc'd for C9H7ClN2O: 194.6.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. additionpoured onto ice slurry
  3. extractionextracted with DCM
  4. customThe organic layer was collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-88e677a76b27494e8ade7635f11cd0e8
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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