3-Chlorophenol → 6,7-Dimethoxyquinazoline

HRID 582437Notes

Reaction equation

HRID 582437 reaction equation
C1COCC1.ClC1C=C(O)C=CC=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1>CCOC(C)=O>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][N:16]=[CH:15]2

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 8028TetrahydrofuranHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 30316616,7-Dimethoxyquinazoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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

Sources & evidence

ORD record
ord-26ca68e09e1e49fea8af7e225e160e2f
Source dataset
uspto-grants-1999_07
Patent number
USRE036256

Reaction notes

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