Water → HCID 22132707, compound

HRID 1857184Notes

Reaction equation

HRID 1857184 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:26]=[C:27]=[O:28])[CH2:24][CH3:25].O>CN(C)C=O>[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:17]=[CH:18][C:19]([NH:22][C:27]([NH:26][CH2:23][CH2:24][CH3:25])=[O:28])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 61033Propyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132707HCID 22132707, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) was dissolved in N,N-dimethylformamide (3 ml), propyl isocyanate (0.2 ml) was added, and the admixture was stirred at 80° C. for 24 hours. Water was added to the reaction mixture, the admixture 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 59 mg of the title compound (yield: 84%).

Workup

  1. extractionthe admixture 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-2d325ec3ef834fc5835f4281c3add501
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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