Diisopropylaniline → HCID 22132620, compound

HRID 1857238Notes

Reaction equation

HRID 1857238 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.[CH:35]([C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH:45]([CH3:47])[CH3:46])[C:39]=1[NH2:40])([CH3:37])[CH3:36].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH:45]([C:41]1[CH:42]=[CH:43][CH:44]=[C:38]([CH:35]([CH3:37])[CH3:36])[C:39]=1[NH:40][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])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 32484DiisopropylanilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132620HCID 22132620, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) was suspended in toluene (5 ml), after the addition of triethylamine (1 ml), triphosgene (53 mg) was added, and the admixture was refluxed with heat for 8 minutes. 2,6-Diisopropylaniline (0.05 ml) was added to the reaction mixture, and the admixture was refluxed with heat for 15 minutes. 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 69 mg of the title compound (yield: 76%).

Workup

  1. additionwas added
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 8 minutes
  4. temperaturethe admixture was refluxed
  5. temperaturewith heat for 15 minutes
  6. extractionthe reaction mixture was extracted 2 times with ethyl acetate
  7. washthe organic layer was then washed with brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was removed by reduced-pressure distillation
  10. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-b090a467434a4ce1a3deb563b9492d42
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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