Methanol → HCID 57742487, compound

HRID 2266420Notes

Reaction equation

HRID 2266420 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]([O: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.CO.[OH-].[Li+]>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:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[C:8]2[O:26][CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68781739HCID 68781739, compound

Product 1

HCID 57742487HCID 57742487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [8-chloro-3-(4-chlorobenzyl)-4-methoxy-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.059 g), methanol (2.0 mL), saturated aqueous lithium hydroxide solution (0.25 mL) and water (0.4 mL) was stirred at room temperature for 15 hours, The methanol was removed under reduced pressure and the pH of the residue adjusted to 1 by the addition of 1.0 M aqueous hydrochloric acid. Purification by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water (20% to 80% of organic modifier) gave title compound as a yellow solid, 0.060 g.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 1 by the addition of 1.0 M aqueous hydrochloric acid
  3. customPurification by preparative reverse-phase
  4. customover 30 minutes

Sources & evidence

ORD record
ord-de7d44cdc45540b584fd0780b03a0ebe
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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