Water → HCID 19799551, compound

HRID 2081283Notes

Reaction equation

HRID 2081283 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([O:27]CC)=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O>CO>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:15][CH:16]=2)[N:8]=[C:7]([C:25]([OH:27])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19799556HCID 19799556, compound

Product 1

HCID 19799551HCID 19799551, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]pyrazole-3-carboxylate (5.75 g) in methanol (100 ml) was added 2N-NaOH (15 ml) and the mixture was allowed to stand at room temperature for 2 hours. Water (10 ml) was added and methanol was evaporated under reduced pressure. The mixture was made acidic by addition of 2N-HCl, followed by extraction with ether. The organic layer was washed with water (20 ml×2), dried, and concentrated under reduced pressure, to give a colorless syrup. The syrup was recrystallized from chloroform to give colorless crystals (4.3 g, 81%).

Workup

  1. custommethanol was evaporated under reduced pressure
  2. additionThe mixture was made acidic by addition of 2N-HCl
  3. extractionfollowed by extraction with ether
  4. washThe organic layer was washed with water (20 ml×2)
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give a colorless syrup
  8. customThe syrup was recrystallized from chloroform

Sources & evidence

ORD record
ord-ff204abae79c48afb334523d1ab3a03a
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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