Ethanol → HCID 57742497, compound

HRID 2266637Notes

Reaction equation

HRID 2266637 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[C:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:10]([CH3:16])=[N:11]2.C(O)C.[OH-].[Li+]>O>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:9]2[C:10]([CH3:16])=[N:11][C:12]3[C:7]([CH:8]=2)=[C:6]([O:5][CH2:4][C:3]([OH:25])=[O:2])[CH:15]=[CH:14][CH:13]=3)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 68782253HCID 68782253, compound

Product 1

HCID 57742497HCID 57742497, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [3-(4-chlorobenzyl)-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.11 g), ethanol (6.0 mL), water (2.0 mL) and saturated aqueous lithium hydroxide solution (2.0 mL) was stirred at room temperature for 5 hours. The ethanol was removed under reduced pressure and the pH of the residue adjusted to 4 by the addition of glacial acetic acid. The resulting precipitate was collected by filtration, washed with water and purification by preparative reverse-phase HPLC using a gradient over 37 minutes of acetonitrile in water (20% to 95% of organic modifier) gave title compound as a yellow gum, 0.028 mg.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 4 by the addition of glacial acetic acid
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water and purification by preparative reverse-phase
  5. customover 37 minutes

Sources & evidence

ORD record
ord-e893195b10884a04abbdb3e44aff1745
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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