Potassium Carbonate → 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

HRID 491671Notes

Reaction equation

HRID 491671 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC([O-])(C)C.[K+].Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][N:20]=[C:19]2[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 37588824-Amino-3-NitrophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-amino-3-nitrophenol (0.8 g, 5.34 mmol, 1.2 eq) in DMSO (3.8 mL, 5×) was treated with KOt-Bu (0.6 g, 5.34 mmol, 1.2 eq), and the mixture was stirred at RT for 2 h. The contents were treated with 4-chloro-6,7-dimethoxyquinazoline (1.0 g, 4.45 mmol, 1.0 eq) and K2CO3 (0.33 g, 2.4 mmol, 0.53 eq) then heated at 110° C. for 16 h. The mixture was cooled to RT, diluted with EtOAc and washed with NaHCO3 (sat). To remove the emulsion, the mixture was filtered through Celite, then the organic layer was washed with brine, 1N NaOH, then brine again. The organic portion was dried with Na2SO4, filtered and evaporated to give the title compound as a brown solid. MS(MH+)=343.1; Calc'd 342.31 for C16H14N4O5.

Workup

  1. temperaturethen heated at 110° C. for 16 h
  2. temperatureThe mixture was cooled to RT
  3. washwashed with NaHCO3 (sat)
  4. customTo remove the emulsion
  5. filtrationthe mixture was filtered through Celite
  6. washthe organic layer was washed with brine, 1N NaOH
  7. dry with materialThe organic portion was dried with Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4424411067454d5a8c4cc27aa1073154
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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