Ethanol → HCID 57742508, compound

HRID 2266446Notes

Reaction equation

HRID 2266446 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[CH:8]=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.C(O)C.[OH-].[Li+]>O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:26])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 68782705HCID 68782705, compound

Product 1

HCID 57742508HCID 57742508, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [8-chloro-3-(4-chlorobenzyl)-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.10 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 an off-white solid, 0.039 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-57673a0bc16241bf8f5c885b851e85ab
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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