Sodium Hydroxide → 1'H,2H-[3,3'-bipyrazole]-5-carboxylic acid

HRID 1409348Notes

Reaction equation

HRID 1409348 reaction equation
[NH:1]1[C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]([C:11]2[NH:12][N:13]=[CH:14][CH:15]=2)=[N:2]1.[OH-].[Na+]>C(O)C>[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]([C:11]2[NH:12][N:13]=[CH:14][CH:15]=2)=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70981238ethyl 1'H,2H-[3,3'-bipyrazole]-5-carboxylate

Product 1

HCID 179307531'H,2H-[3,3'-bipyrazole]-5-carboxylic acidYield 157.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1H,2′H-3,3′-bipyrazole-5-carboxylate (1.959 mmol, 0.404 g) was dissolved in ethanol (5 ml) and cooled in an ice bath. NaOH 1 M solution (1.959 mmol, 4 ml) was slowly added. The solution was heated to 60° C. for 1 h. Ethanol was removed under vacuum and the residue was diluted with tert-butyl methyl ether. The solution was again cooled with an ice bath and acidified with 2 N HCl solution. The solution was allowed to warm to ambient temperature and stirred overnight. Water and DCM was added and the phases were separated. Both phases were evaporated and combined. 0.551 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 6.70 (d, 1H), 7.04 (s, 1H), 7.77 (d, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. customEthanol was removed under vacuum
  3. additionthe residue was diluted with tert-butyl methyl ether
  4. temperatureThe solution was again cooled with an ice bath
  5. temperatureto warm to ambient temperature
  6. additionWater and DCM was added
  7. customthe phases were separated
  8. customBoth phases were evaporated

Sources & evidence

ORD record
ord-ce013e2a37104dfca7d39c3e468768a0
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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