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

HRID 522111Notes

Reaction equation

HRID 522111 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[CH:33]=[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].[Li+].[OH-].O.Cl>>[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[CH:33]=[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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 118497071ethyl 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1184970355-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidYield 83.3%

Procedure

To a solution of ethyl 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Example 124, 2.5 g, 5.19 mmol) in industrial methylated spirit (50 mL) was added a 1M LiOH solution in water (26 mL, 26 mmol) and the reaction was stirred at room temperature for 3 hours. The reaction was acidified with 2M HCl (aq) (13 mL, 26 mmol) to afford a precipitate that was filtered and washed with industrial methylated spirit to afford the title compound (1.96 g, 83%).

Workup

  1. customto afford a precipitate that
  2. filtrationwas filtered
  3. washwashed with industrial methylated spirit

Sources & evidence

ORD record
ord-9668f7d3e9cb46089b523b021714e6c9
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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