Lithium Hydroxide → HCID 16659925, compound

HRID 2266573Notes

Reaction equation

HRID 2266573 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[F:29])[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:9]2[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11][C:12]3[C:7]([C:8]=2[CH3:30])=[C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[C:23]([F:29])[CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68782375HCID 68782375, compound

Product 1

HCID 16659925HCID 16659925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [3-(4-chloro-2-fluorobenzyl)-2-difluoromethoxy-8-fluoro-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.094 g), tetrahydrofuran (10 mL) and 1.0 M aqueous lithium hydroxide solution (0.22 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue diluted with water. The pH of this mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure to afford title compound, 0.090 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. additionThe pH of this mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-637818da692749538caa3cb85e0b195b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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