N-Methylaniline → HCID 22132788, compound

HRID 1857190Notes

Reaction equation

HRID 1857190 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.[CH3:35][NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:35][N:36]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[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]

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132788HCID 22132788, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (72 mg) was suspended in toluene (7 ml), triphosgene (52 mg) was added, and the admixture was refluxed with heat for 3 hours. N-Methylaniline (0.05 ml) 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 48 mg of the title compound (yield: 46%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 3 hours
  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-3708b2b9655e493381d9ce74284ae49c
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…