Acetic Acid → HCID 25096078, compound

HRID 1944313Notes

Reaction equation

HRID 1944313 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:33])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:24][CH:23]=1)[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.[OH-].[Na+].C(O)(=O)C>CO.O>[F:20][CH:18]([F:19])[O:17][C:10]1[C:9]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:24][CH:23]=2)=[C:8]([CH3:33])[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:34])=[O:2])[N:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67455340HCID 67455340, compound

Product 1

HCID 25096078HCID 25096078, compoundYield 8.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of [2-difluoromethoxy-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.43 g) in methanol (7.0 mL) and water (0.7 mL) was treated with 5.0M aqueous sodium hydroxide solution (0.36 mL), and the resulting mixture was stirred at room temperature for 1.5 hours. The mixture was acidified by the addition of glacial acetic acid, diluted with water and then extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel gave title compound as a white solid (0.034 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-28f45256e6b64081be33cde80e1d8a5b
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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