Water → 1-{3-[7-(2,3-Dihydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone

HRID 228997Notes

Reaction equation

HRID 228997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14]C1CO1)[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[C:20]([C:29](=[O:31])[CH3:30])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.F[C:33](F)(F)[C:34]([OH:36])=O.[OH-:39].[Na+].O>C(Cl)Cl>[OH:39][CH:33]([CH2:34][OH:36])[CH2:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:18][C:19]3[C:20]([C:29](=[O:31])[CH3:30])=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 577565081-[3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone2×

Product 1

HCID 577564701-{3-[7-(2,3-Dihydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone (compound 394) (150 mg) was dissolved in methylene chloride (2 ml) to prepare a solution which was brought to 0° C. Trifluoroacetic acid (1 ml) was added to the solution, and the mixture was stirred at 0° C. for 30 min. The mixture was then stirred at room temperature for 4 hr. The reaction solution was brought to 0° C. and was stirred. The reaction solution was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was 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 (140 mg, yield 90%).

Workup

  1. customto prepare a solution which
  2. customwas brought to 0° C
  3. stirringThe mixture was then stirred at room temperature for 4 hr
  4. customwas brought to 0° C.
  5. stirringwas stirred
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was then washed with saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-625c838421ad491893e949910710dd16
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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