Hydrochloric Acid → [8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methyl-quinolin-5-yloxy]acetic Acid

HRID 2266474Notes

Reaction equation

HRID 2266474 reaction equation
C[O:2][C:3](=[O:30])[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][CH:27]([F:29])[F:28])=[C:9]([S:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.[OH-].[Na+].Cl>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([S:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[C:8]2[O:26][CH:27]([F:28])[F:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68780463[8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

Product 1

HCID 57742534[8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methyl-quinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.044 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous sodium hydroxide solution (0.15 mL) was stirred at room temperature for 1 hour. The solution was acidified by the addition of 1.0 M aqueous hydrochloric acid and the solvent removed under reduced pressured. The residue was diluted with ethyl acetate and this mixture washed with water and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting solid washed with dichloromethane and dried to afford title compound, 0.024 g.

Workup

  1. customthe solvent removed
  2. additionThe residue was diluted with ethyl acetate
  3. washthis mixture washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe resulting solid washed with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-f3cd9a5d3112483b944eb766f8fd4a39
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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