Hydrochloric Acid → 1-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid

HRID 1294842Notes

Reaction equation

HRID 1294842 reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:7]=1)=[O:5])C.Cl>[OH-].[K+].CCO>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:8]1[C:9]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[C:10]([CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 587609561-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 218687991-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acidYield 133.7%

Reagents, catalysts & solvents 1

HCID 21946426Potassium hydroxide ethanolSolvent

Procedure

A solution of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-4c (32 mg, 0.074 mmol) in a 1:4 solution of 1M KOH/EtOH (10 ml) was stirred at 50° C. for 6 hours and at 37° C. for 72 hours. The reaction mixture was treated with conc. HCl until the pH of the solution was approximately 1 and then concentrated in vacuo. The residue was diluted with EtOH and filtered. The filtrate was concentrated under vacuum to give I-4a as a white solid (40 mg, 100%): +APCI MS (M+1) 404.1.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOH
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-23a01d5068c443f6afbe04d10760b8e4
Source dataset
uspto-grants-2007_07
Patent number
US07241788B2

Reaction notes

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