Water → HCID 22132794, compound

HRID 1857186Notes

Reaction equation

HRID 1857186 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.[CH2:23]([N:29]=[C:30]=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>CN(C)C=O>[CH2:23]([NH:29][C:30]([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:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 75659Hexyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132794HCID 22132794, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was dissolved in N,N-dimethylformamide (3 ml), hexyl isocyanate (0.2 ml) was added, and the admixture was stirred at 60° C. for 15 hours. After the addition of water, 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 63 mg of the title compound (yield: 84%).

Workup

  1. extractionthe reaction mixture was extracted 2 times with ethyl acetate
  2. washthe organic layer was then washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-6f5bd15f514b4bb9bff429c21116cddc
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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