1,4-Benzodioxan-6-ylamine → HCID 22132650, compound

HRID 1857188Notes

Reaction equation

HRID 1857188 reaction equation
[CH2:1]1[CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.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.C(N(CC)CC)C>[CH2:1]1[CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:13]([NH:45][C:42]3[CH:41]=[CH:40][C:39]([O:38][C:29]4[C:28]5[C:33](=[CH:34][C:35]([O:36][CH3:37])=[C:26]([O:25][CH3:24])[CH:27]=5)[N:32]=[CH:31][CH:30]=4)=[CH:44][CH:43]=3)=[O:15])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 891481,4-Benzodioxan-6-ylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132650HCID 22132650, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

3,4-Ethylenedioxyaniline (80 mg) was dissolved in toluene (5 ml), triethylamine (0.5 ml) and then triphosgene (50 mg) were added, and the admixture was refluxed with heat for 1 hour. 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was added, and the admixture was refluxed with heat for 100 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 62 mg of the title compound (yield: 74%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 1 hour
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 100 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-00ba0294f9ad4ceaaf500faec2805706
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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