Hydrochloric Acid → 5-(2,4-dichloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

HRID 522109Notes

Reaction equation

HRID 522109 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([O:20]CC)=[O:19])[CH:8]=1)=[O:5].[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118497121ethyl 5-(2,4-dichloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1184970555-(2,4-dichloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of ethyl 5-(2,4-dichloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Example 122A, 58.3 g, 0.117 mol) in IMS (580 mL), was added 2M aqueous sodium hydroxide solution (176 mL, 0.352 mol) and the reaction stirred at room temperature for 5 hours. The reaction mixture was diluted with water (600 mL) and acidified to pH1 with hydrochloric acid solution (40 mL, 36%). The resulting solid was filtered and washed with water (50 mL) to give the title compound as a white solid (53.1 g, 97%).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-ff8bc3eb5b5c427ca272673055c1fd13
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

Loading…