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Methanol → [3-(2,4-dichlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid

HRID 2266567
Notes
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Reaction equation

HRID 2266567 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:28][CH:29]([F:31])[F:30])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])[C:10]([CH2:17][CH3:18])=[N:11]2.CO.O.[OH-].[Na+]>C(O)(=O)C>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[CH2:19][C:9]1[C:10]([CH2:17][CH3:18])=[N:11][C:12]2[C:7]([C:8]=1[O:28][CH:29]([F:30])[F:31])=[C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])[CH:15]=[CH:14][C:13]=2[F:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68782112HCID 68782112, compound

Product 1

HCID 16659924[3-(2,4-dichlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Procedure

A solution of [3-(2,4-dichlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.17 g), methanol (6 mL), water (0.3 mL) and 5.0 M aqueous sodium hydroxide solution (0.15 mL) was stirred at room temperature for 1 hour. The pH of the solution was adjusted to 5 by the addition of glacial acetic acid and the solvent removed under reduced pressure. The residue was diluted with water and the solid collected by filtration. Purification by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (1:0 to 3:1 by volume) gave title compound as a white solid, 0.030 g.

Workup

  1. customthe solvent removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationthe solid collected by filtration
  4. customPurification by column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (1:0 to 3:1 by volume)

Sources & evidence

ORD record
ord-fceea7bbef5e4f56a14df24effbfdd1d
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858640B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes