3-Chlorophenol → 6,7-Dimethoxyquinazoline

HRID 263952Notes

Reaction equation

HRID 263952 reaction equation
[H-].[Na+].ClC1C=C(O)C=CC=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1.CCOC(C)=O>C1COCC1>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[N:15]=[CH:14][N:13]=[CH:12]2

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 30316616,7-Dimethoxyquinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

THF (5 ml) and NaH (60% disp in oil, approx. 28 mg) is added to a dry flask maintained under inert atmosphere at room temperature. m-Chlorophenol (0.09 g) is added as a soin. In THF (1 mL) and stirring Is continued until the solution became clear. 4-Chloro-6,7-dimethoxyquinazoline is added all at once (as the solid) and stirring was maintained overnight at RT. The solution is partitioned between CH2CL2 and 5% NaOH. The organic layer is washed with brine, dried (Na2SO4) and concentrated. Flash column chromatography (40% EtOAc/Hex) provided the pure compound. An analytical sample is obtained by recrystallization from EtOAc/Hex to provide 4-m-chlorophenoxy)-6,7-dimethoxyquinazoline (0.05 g, white needles, m.p. 152°-153° C.

Workup

  1. temperaturewas maintained overnight at RT
  2. customThe solution is partitioned between CH2CL2 and 5% NaOH
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash column chromatography (40% EtOAc/Hex) provided the pure compound

Sources & evidence

ORD record
ord-933dd18018cd41ea86500644dee26b38
Source dataset
uspto-grants-1997_07
Patent number
US05646153

Reaction notes

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