3-Chlorophenol → 6,7-Dimethoxyquinazoline

HRID 374477Notes

Reaction equation

HRID 374477 reaction equation
ClC1C=C(O)C=CC=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1.CCOC(C)=O>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:22][CH3:23])[N:13]=[CH:12][N:11]=[CH:10]2

Participants

5

Reactant 3

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

Product 1

HCID 30316616,7-Dimethoxyquinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 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-40e9616002c04febbcb89227ecb533d8
Source dataset
uspto-grants-1996_01
Patent number
US05480883

Reaction notes

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