Methanol → [7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic Acid

HRID 2266450Notes

Reaction equation

HRID 2266450 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]2[C:6]=1[C:7]([CH3:25])=[C:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:9]([CH3:16])=[N:10]2.CO.O.[OH-].[Li+]>C(O)(=O)C>[Cl:15][C:13]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:25])=[C:8]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[C:9]([CH3:16])=[N:10]2)=[C:5]([CH2:4][C:3]([OH:26])=[O:2])[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 68782352[7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic Acid Methyl Ester

Product 1

HCID 57742513[7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of [7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic acid methyl ester (0.24 g), methanol (10 mL), water (2.0 mL) and saturated aqueous lithium hydroxide solution (1.0 mL) was stirred at room temperature for 17 hours. The pH of the solution was adjusted to 5 by the addition of glacial acetic acid and the methanol removed under reduced pressure. The resulting precipitate was collected by filtration and washed with water. Crystallisation of the solid from ethyl, acetate gave title compound as a fluffy white solid, 0.16 g

Workup

  1. customthe methanol removed under reduced pressure
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customCrystallisation of the solid from ethyl, acetate

Sources & evidence

ORD record
ord-fb659d0830a646f580525d3347b4a0ac
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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