4-Aminobenzophenone → HCID 22132709, compound

HRID 1857185Notes

Reaction equation

HRID 1857185 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.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:35][C:36]1[CH:49]=[CH:48][C:39]([C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:41])=[CH:38][CH:37]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[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:17]=[CH:18][C:19]([NH:22][C:24]([NH:35][C:36]2[CH:37]=[CH:38][C:39]([C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:41])=[CH:48][CH:49]=2)=[O:26])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 143464-AminobenzophenoneHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132709HCID 22132709, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) was suspended in toluene (5 ml), triphosgene (53 mg) was added, and the admixture was refluxed with heat for 20 minutes. 4-Aminobenzophenone (85 mg) was added to the reaction mixture, and the admixture was refluxed for 1 hour with heat. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, 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 purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 19 mg of the title compound (yield: 21%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 20 minutes
  3. temperaturethe admixture was refluxed for 1 hour
  4. temperaturewith heat
  5. extractionthe reaction mixture was extracted 2 times with ethyl acetate
  6. washthe organic layer was then washed with brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was removed by reduced-pressure distillation
  9. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-1891bb0a5d374e9fa831d082cd3a2d8b
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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