Ethyl 3-aminobenzoate → HCID 22132740, compound

HRID 1857248Notes

Reaction equation

HRID 1857248 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.[NH2:35][C:36]1[CH:37]=[C:38]([CH:44]=[CH:45][CH:46]=1)[C:39]([O:41][CH2:42][CH3:43])=[O:40].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:42]([O:41][C:39]([C:38]1[CH:37]=[C:36]([NH:35][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:46]=[CH:45][CH:44]=1)=[O:40])[CH3:43]

Participants

7

Reactant 4

HCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132740HCID 22132740, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (131 mg) was dissolved in toluene (10 ml) with heat, after the addition of triethylamine (2 ml), triphosgene (213 mg) was added, and the admixture was refluxed with heat for 2 minutes. Ethyl 3-aminobenzoate (0.1 ml) was added to the reaction mixture, and the admixture was refluxed with heat for 7 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 214 mg of the title compound (yield: 100%).

Workup

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

Sources & evidence

ORD record
ord-49e9f40ffcde4f8a89849ecb55e2e603
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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