Hydrochloric Acid → HCID 57742516, compound

HRID 2266438Notes

Reaction equation

HRID 2266438 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:26])=[C:9]([O: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-].[Na+].Cl>O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:27])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([O:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[C:8]2[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68782473HCID 68782473, compound

Product 1

HCID 57742516HCID 57742516, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [8-chloro-3-(4-chlorophenoxy)-2,4-dimethylquinolin-5-yloxy]acetic acid methyl ester (0.20 g), methanol (5.0 mL), water (1.0 mL) and 5.0 M aqueous sodium hydroxide solution (1.0 mL) was stirred at room temperature for 3 hours. The pH of the solution was adjusted to 1 by the addition of 1.0 M hydrochloric acid and the methanol removed under reduced pressure. The residue was purified by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water (40% to 98% of organic modifier) to afford title compound as a yellow-green solid, 0.025 g.

Workup

  1. customthe methanol removed under reduced pressure
  2. customThe residue was purified by preparative reverse-phase
  3. customover 30 minutes

Sources & evidence

ORD record
ord-bf0ff0fc3ce14ffcbcd657c39096820a
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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