3-Aminophenol → HCID 22132761, compound

HRID 1857293Notes

Reaction equation

HRID 1857293 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[NH2:35][C:36]1[CH:37]=[C:38]([OH:42])[CH:39]=[CH:40][CH:41]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[OH:42][C:38]1[CH:37]=[C:36]([NH:35][C:27]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)=[O:33])[CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 115683-AminophenolHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132761HCID 22132761, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (115 mg) was dissolved in toluene (12 ml) with heat, after the addition of triethylamine (2 ml), triphosgene (113 mg) was added, and the admixture was refluxed with heat for 2 minutes. 3-Aminophenol (73 mg) was added to the reaction mixture, and the admixture was refluxed with heat for 10 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted with chloroform, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was washed with chloroform and filtered to obtain 95 mg of the title compound (yield: 60%).

Workup

  1. temperaturewith heat
  2. additionwas added
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 2 minutes
  5. temperaturethe admixture was refluxed
  6. temperaturewith heat for 10 minutes
  7. extractionthe reaction mixture was extracted with chloroform
  8. washthe organic layer was then washed with brine
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was removed by reduced-pressure distillation
  11. washthe resulting residue was washed with chloroform
  12. filtrationfiltered

Sources & evidence

ORD record
ord-3f9d94094847449c8e43ea6f16be4b7d
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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