Potassium Carbonate → HCID 22030696, compound

HRID 453999Notes

Reaction equation

HRID 453999 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[N:30]2)=[CH:25][CH:24]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[N:30]2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 22030696HCID 22030696, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6,7-Dimethoxy-3,4-dihydroquinazolin-4-one (290 mg, 1.4 mmol) was suspended in thionyl chloride (5 ml) and DMF (2 drops) and heated at reflux for 2 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times to give 4-chloro-6,7-dimethoxyquinazoline. A mixture of the crude 4-chloro-6,7-dimethoxyquinazoline, potassium carbonate (970 mg, 7 mmol) and 7-hydroxyquinoline (235 mg, 1.62 mmol) in DMF (10 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature overnight. The reaction mixture was treated with 1M aqueous sodium hydroxide solution and stirred at ambient temperature for a few minutes. The reaction mixture was extracted with ethyl acetate (×4) and the organic extracts washed with water and brine. The organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum. The residue was triturated with ethyl acetate and then recrystallised from hot ethyl acetate to give 6,7-dimethoxy-4-(quinolin-7-yloxy)quinazoline (110 mg, 24%) as a white solid.

Workup

  1. temperatureto cool to ambient temperature overnight
  2. stirringstirred at ambient temperature for a few minutes
  3. extractionThe reaction mixture was extracted with ethyl acetate (×4)
  4. washthe organic extracts washed with water and brine
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customThe residue was triturated with ethyl acetate
  9. customrecrystallised from hot ethyl acetate

Sources & evidence

ORD record
ord-89435aa59db141d2b9d4c0a5fb59849a
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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