Methanol → HCID 57742505, compound

HRID 2266458Notes

Reaction equation

HRID 2266458 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH2:26][CH3:27])=[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:30][C:31](=[O:56])[CH2:32][O:33][C:34]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]2[C:35]=1[C:36]([CH3:55])=[C:37]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1)[C:38]([CH2:45][CH3:46])=[N:39]2.CO.[OH-].[Li+]>C(O)(=O)C.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:28])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:8]2[CH2:26][CH3:27].[Cl:44][C:41]1[CH:42]=[CH:43][C:34]([O:33][CH2:32][C:31]([OH:56])=[O:30])=[C:35]2[C:40]=1[N:39]=[C:38]([CH2:45][CH3:46])[C:37]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1)=[C:36]2[CH3:55]

Participants

8

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68783204HCID 68783204, compoundHCID 68783255HCID 68783255, compound

Product 2

HCID 57742505HCID 57742505, compoundHCID 57742531HCID 57742531, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of [8-chloro-3-(4-chlorobenzyl)-4-ethyl-2-methylquinolin-5-yloxy]acetic acid methyl ester and [8-chloro-3-(4-chlorobenzyl)-2-ethyl-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.26 g), methanol (15 mL), water (1.5 mL) and saturated aqueous lithium hydroxide solution (1.5 mL) was stirred at room temperature for 3 hours. The pH of the solution was adjusted to 4 by the addition of glacial acetic acid and the methanol removed under reduced pressure. The resulting precipitate was collected by filtration and purified by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water (40% to 98% of organic modifier) to afford [8-chloro-3-(4-chlorobenzyl)-4-ethyl-2-methylquinolin-5-yloxy]acetic acid as a yellow foam, 0.049 g and [8-chloro-3-(4-chlorobenzyl)-2-ethyl-4-methylquinolin-5-yloxy]acetic acid as a yellow foam, 0.10 g.

Workup

  1. customthe methanol removed under reduced pressure
  2. filtrationThe resulting precipitate was collected by filtration
  3. custompurified by preparative reverse-phase
  4. customover 30 minutes

Sources & evidence

ORD record
ord-24d45d0f772e4669b62659e04e894080
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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