Ethanol → 4-Carboxymethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid

HRID 1921250Notes

Reaction equation

HRID 1921250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([OH:22])=[O:21])[C:9]=2CC#N)=[CH:4][CH:3]=1.[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>O>[C:28]([CH2:29][C:9]1[C:10]([C:20]([OH:22])=[O:21])=[N:11][N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([OH:26])=[O:30]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 591463351-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(cyanomethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 591463474-Carboxymethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-cyanomethyl-1H-pyrazole-3-carboxylic acid [B1] (30 g, 0.8 mol) were added sodium hydroxide (19 g, 4.8 mol), ethanol (250 ml) and water (150 ml). The reaction mixture was heated to reflux over night. The heating was removed and the reaction mixture was allowed to reach room temperature. The formed precipitate was collected and washed with ethanol and dried in an exicator over night. The sodium salt was dissolved in water (400 ml) and HCl (4N) was added during extensively stirring, to avoid forming a gum, and the precipitate is collected and dried in a vacuum oven, yielding 27 g (0.7 mol, 86%) of 4-Carboxymethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid [G1]. LCMS (method A): RT=2.1 min; ES+=390.9 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux over night
  3. customThe heating was removed
  4. customto reach room temperature
  5. customThe formed precipitate was collected
  6. washwashed with ethanol
  7. customdried in an exicator over night
  8. dissolutionThe sodium salt was dissolved in water (400 ml)
  9. additionHCl (4N) was added
  10. customto avoid forming a gum
  11. customthe precipitate is collected
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-444a900e113b4cf3bdebda8fdf43bbed
Source dataset
uspto-grants-2012_05
Patent number
US08173680B2

Reaction notes

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