Trifluoroacetic acid → 3-[7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-yloxy]-propane-1,2-diol

HRID 229023Notes

Reaction equation

HRID 229023 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[C:15]([CH3:24])=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[O:25][CH2:26][CH:27]1[CH2:29][O:28]1.FC(F)(F)C(O)=[O:33].[OH-].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[C:15]([CH3:24])=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[O:25][CH2:26][CH:27]([OH:33])[CH2:29][OH:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 230782567-Methoxy-4-(2-methyl-quinolin-3-yloxy)-6-oxiranylmethoxy-quinoline

Product 1

HCID 577563543-[7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-yloxy]-propane-1,2-diolYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-6-oxiranylmethoxy-quinoline (59 mg) was dissolved in dichloromethane (2 ml) to prepare a solution. Trifluoroacetic acid (2 ml) was added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 4 hr. The reaction solution was made alkaline by the addition of 1 N sodium hydroxide, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (18 mg, yield 29%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-adeeba09ba2e4bbb8d3131146e0f4c40
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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