Sodium Hydroxide → HCID 16659921, compound

HRID 2266553Notes

Reaction equation

HRID 2266553 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:30])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.[OH-].[Na+]>CO>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH2:21][C:9]1[C:10]([O:17][CH:18]([F:19])[F:20])=[N:11][C:12]2[C:7]([C:8]=1[CH3:30])=[C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])[CH:15]=[CH:14][C:13]=2[F:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68782425HCID 68782425, compound

Product 1

HCID 16659921HCID 16659921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [3-(2,4-dichlorobenzyl)-2-difluoromethoxy-8-fluoro-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.071 g), methanol (10 mL), and 5.0 M aqueous sodium hydroxide solution (0.15 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the pH of the residue adjusted to 4 by the addition of glacial acetic acid. The mixture was diluted in ethyl acetate, washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and methanol (1:0 to 1:1 by volume) to afford title compound as a white solid, 0.040 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 4 by the addition of glacial acetic acid
  3. additionThe mixture was diluted in ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography on silica gel
  8. washeluting with a mixture of ethyl acetate and methanol (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-f2fba082259a427580490e71677f743b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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