2-Aminophenol → HCID 22132704, compound

HRID 1857292Notes

Reaction equation

HRID 1857292 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:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[OH:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:35][C:27]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:21][CH:20]=1)=[O:33]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132704HCID 22132704, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (105 mg) was dissolved in toluene (10 ml) with heat, after the addition of triethylamine (2 ml), triphosgene (118 mg) was added, and the admixture was refluxed with heat for 2 minutes. 2-Aminophenol (77 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 86 mg of the title compound (yield: 56%).

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-580d674c604f4a83b3aa9944b0bb2a65
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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