3,5-Dimethoxyaniline → HCID 22132730, compound

HRID 1857273Notes

Reaction equation

HRID 1857273 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.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:41]=[C:42]([O:44][CH3:45])[CH:43]=1)[NH2:40].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:45][O:44][C:42]1[CH:41]=[C:39]([NH:40][C:24]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)=[O:26])[CH:38]=[C:37]([O:36][CH3:35])[CH:43]=1

Participants

7

Reactant 4

HCID 663013,5-DimethoxyanilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132730HCID 22132730, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (53 mg) was dissolved in toluene (5 ml) with heat, after the addition of triethylamine (1 ml), triphosgene (101 mg) was added, and the admixture was ref luxed with heat for 4 minutes. 3,5-Dimethoxyaniline (62 mg) was added to the reaction mixture, and the admixture was refluxed with heat for 13 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 85 mg of the title compound (yield: 100%)).

Workup

  1. temperaturewith heat
  2. additionwas added
  3. temperaturewith heat for 4 minutes
  4. temperaturethe admixture was refluxed
  5. temperaturewith heat for 13 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-65c1e779d083416e91927a5a40775b73
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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