Potassium Hydroxide → 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid

HRID 280467Notes

Reaction equation

HRID 280467 reaction equation
[OH-].[K+].[C:3]([C:5]1[N:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=[CH:7][C:6]=1[C:14]([O:16]CC)=[O:15])#[N:4]>C(O)C>[C:3]([C:5]1[N:9]([C:10]([CH3:12])([CH3:13])[CH3:11])[N:8]=[CH:7][C:6]=1[C:14]([OH:16])=[O:15])#[N:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 1636771H-Pyrazole-4-carboxylic acid, 5-cyano-1-(1,1-dimethylethyl)-, ethyl ester

Product 1

HCID 212472685-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Potassium hydroxide (1.7 grams, 0.027 mole) was dissolved in 20 ml of ethanol. This solution was poured into a refluxing solution of 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester, in 50 ml of ethanol. The reaction mixture was heated on a steam bath for five minutes, then poured into ice-water, filtered, and acidified with concentrated hydrochloric acid. The precipitated product was collected and dried, yielding 3.2 grams of 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid (72% yield).

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for five minutes
  2. filtrationfiltered
  3. customThe precipitated product was collected
  4. customdried

Sources & evidence

ORD record
ord-18650eff5c70498eb30a642e0015673d
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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