Lithium Hydroxide → [3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic Acid

HRID 2266429Notes

Reaction equation

HRID 2266429 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([CH3:26])=[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(#N)C.[OH-].[Li+]>O1CCCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:9]2[C:10]([CH3:17])=[N:11][C:12]3[C:7]([C:8]=2[CH3:26])=[C:6]([O:5][CH2:4][C:3]([OH:27])=[O:2])[CH:15]=[C:14]([CH3:16])[CH:13]=3)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 68782119[3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic Acid Methyl Ester

Product 1

HCID 57742515[3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic acid methyl ester (0.045 g), acetonitrile (2.0 mL), tetrahydrofuran (1.0 mL) and 4.0 M aqueous lithium hydroxide solution (2.0 mL) was stirred at room temperature for 2 hours. The organic solvents were removed under reduced pressure and the pH of the residue adjusted to 5-6 by the addition of saturated aqueous sodium dihydrogenphosphate solution. The resulting mixture was extracted with chloroform and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure and trituration of the residue with diethyl ether and then methanol gave title compound, 0.025 g.

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionthe pH of the residue adjusted to 5-6 by the addition of saturated aqueous sodium dihydrogenphosphate solution
  3. extractionThe resulting mixture was extracted with chloroform
  4. dry with materialthe combined extracts dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure and trituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-d2dc3ac01084447e88f3ff4d3aa5ff55
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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