3,4-Dimethoxyaniline → HCID 22132787, compound

HRID 1857187Notes

Reaction equation

HRID 1857187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][C:35]=1[O:36][CH3:37])[N:32]=[CH:31][CH:30]=[C:29]2[O:38][C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:13]([NH:45][C:42]2[CH:41]=[CH:40][C:39]([O:38][C:29]3[C:28]4[C:33](=[CH:34][C:35]([O:36][CH3:37])=[C:26]([O:25][CH3:24])[CH:27]=4)[N:32]=[CH:31][CH:30]=3)=[CH:44][CH:43]=2)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 227703,4-DimethoxyanilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132787HCID 22132787, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-Dimethoxyaniline (42 mg) was dissolved in toluene (5 ml), triphosgene (24 mg) was added, and the admixture was refluxed with heat for 22 minutes. 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was added, and the admixture was refluxed with heat for 18 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 15 mg of the title compound (yield: 18%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 22 minutes
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 18 minutes
  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-af4829f163914add8285389e03cec1ac
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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