Sodium Hydroxide → 3-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid

HRID 872761Notes

Reaction equation

HRID 872761 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[NH:9][N:8]=2)[CH:2]=1.[OH-].[Na+]>C(O)C.C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=2)[CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 575603Ethyl 3-(pyridin-3-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 31597153-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-(pyridin-3-yl)-1H-pyrazole-5-carboxylate (1.577 g, 7.26 mmol) in Ethanol (60 ml) and THF (60 ml) was reacted with 1M NaOH solution (40 ml, 7.26 mmol) and heated to 60° C. for 2 h. The solvents were evaporated under reduced pressure and the residue was diluted with water. The solution was made acidic by the addition of 2 N HCl solution. The resultant mixture was stirred in ice-cold bath for 4 h and the solid precipitated was filtered, dried and weighed. Yield 378 mg. 1H NMR (400 MHz; d6-DMSO): δ 7.39 (m, 2H), 8.21 (d, 1H), 8.53 (bs, 1H), 9.06 (bs, 1H).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. additionThe solution was made acidic by the addition of 2 N HCl solution
  4. customthe solid precipitated
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-481aa490ad6f492e8700759743d0102f
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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