Dimethyl Sulfoxide → 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

HRID 720960Notes

Reaction equation

HRID 720960 reaction equation
[H-].[Na+].CS(C)=O.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].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>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:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroanilineYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60 wt%, 0.20 g) was added to dimethyl sulfoxide (15 ml), and the mixture was stirred at room temperature for 10 min. 4-Amino-3-nitrophenol (0.77 g) was added thereto, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinazoline (1.12 g) was added thereto, and the mixture was stirred at 100° C. for 3 hr. Water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a 1 N aqueous sodium hydroxide solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and methanol was added to the residue to prepare a suspension. The precipitated crystal was collected by suction filtration to give the title compound (1.10 g, yield 64%).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. stirringthe mixture was stirred at 100° C. for 3 hr
  3. extractionfollowed by extraction with chloroform
  4. washThe chloroform layer was then washed with a 1 N aqueous sodium hydroxide solution
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure, and methanol
  7. additionwas added to the residue
  8. customto prepare a suspension
  9. filtrationThe precipitated crystal was collected by suction filtration

Sources & evidence

ORD record
ord-d19066959a644b919181d7a827098a57
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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