Triethylamine → 4-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol

HRID 1727854Notes

Reaction equation

HRID 1727854 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:37][CH3:38])C1C=CC=CC=1.C(N(CC)CC)C.[H][H]>CN(C)C=O.[OH-].[Pd+2].[OH-]>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][C:13]3[C:12]4[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:37][CH3:38])[CH:11]=4)[N:16]=[CH:15][CH:14]=3)=[CH:21][CH:22]=2)=[CH:32][CH:31]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57567431[4-(7-Benzyloxy-6-methoxy-4-quinolyloxy)phenyl](4-tert-butylphenyl)amine2×HCID 178418361HCID 178418361, compound

Product 1

HCID 1357802514-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-olYield 62.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolvent

Procedure

[4-(7-Benzyloxy-6-methoxy-4-quinolyloxy)phenyl](4-tert-butylphenyl)amine (starting compound 2) (400 mg) was dissolved in N,N-dimethylformamide (10 ml) to prepare a solution. Triethylamine (2 ml) and 20% palladium hydroxide (0.58 g) were then added to the solution, and the mixture was stirred in a hydrogen atmosphere at room temperature overnight. The insolubles were removed by filtration, and the solvent was then removed by evaporation under the reduced pressure. Water and ethyl acetate were added to the crude, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (205 mg, yield 62%).

Workup

  1. customto prepare a solution
  2. customThe insolubles were removed by filtration
  3. customthe solvent was then removed by evaporation under the reduced pressure
  4. additionWater and ethyl acetate were added to the crude
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialwas dried over sodium sulfate
  8. customThe solvent was removed by evaporation under the reduced pressure
  9. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cc334c49fc3641c78fb717f4b08cbce1
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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