Sodium Hydroxide → HCID 19004320, compound

HRID 2225732Notes

Reaction equation

HRID 2225732 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[O:25]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:9][CH:10]=1)[C:3]([OH:26])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54406088HCID 54406088, compound

Product 1

HCID 19004320HCID 19004320, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of alpha-oxo-4-[[2-(4-quinolyloxy)ethyl]oxy]benzeneacetic acid methyl ester (0.50 g) in hot methanol (10 mL) was treated with 1N sodium hydroxide (4.0 mL) and diluted with water. The organic solvent was removed under vacuum and the residue was dissolved in water and chilled in ice. Cold 2N hydrochloric acid (2.0 mL) was added dropwise and the product was allowed to crystallize and was filtered, washed with water and dried to give 0.477 g of alpha-oxo-4-[[2-(4-quinolyloxy)ethyl]oxy]benzeneacetic acid as a colorless solid, mp 271° C. with decomposition.

Workup

  1. customThe organic solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in water
  3. temperaturechilled in ice
  4. additionCold 2N hydrochloric acid (2.0 mL) was added dropwise
  5. customto crystallize
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ebe60f07efa34517a161fd3594dfb38c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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