Sodium Hydroxide → 5-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid

HRID 2054985Notes

Reaction equation

HRID 2054985 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:15][CH2:16][C:17]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:18][C:19]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[O:29][CH3:30])([CH3:21])[CH3:20])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[F:28][C:26]1[CH:25]=[CH:24][C:23]([O:29][CH3:30])=[C:22]([C:19]([CH3:20])([CH3:21])[CH2:18][C:17]([OH:35])([C:31]([F:33])([F:32])[F:34])[CH2:16][NH:15][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[CH:13]=[CH:14][C:5]([C:3]([OH:4])=[O:2])=[N:6]3)[CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 207862315-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid methyl ester

Product 1

HCID 219488185-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution that consists of 60 mg (0.12 mmol) of 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid methyl ester in 10 ml of methanol is mixed with 0.5 ml (0.5 mmol) of 1N sodium hydroxide solution. After 2.5 hours, the solvent is removed in a vacuum, and the residue is purified on silica gel with dichloromethane-methanol (6-25%). 47 mg (82% of theory) is obtained.

Workup

  1. customthe solvent is removed in a vacuum
  2. customthe residue is purified on silica gel with dichloromethane-methanol (6-25%)
  3. custom47 mg (82% of theory) is obtained

Sources & evidence

ORD record
ord-1e6a09162e5745ec995fceba8a4994cf
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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