Sodium Hydroxide → 2-Ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester

HRID 908212Notes

Reaction equation

HRID 908212 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][CH3:17])[N:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:5])C.[OH-].[Na+]>>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[N:8][N:7]([CH2:16][CH3:17])[C:6]=1[C:4]([OH:5])=[O:3])=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67041773HCID 67041773, compound

Product 1

HCID 670418082-Ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl esterYield 81%

Procedure

2-Ethyl-2H-pyrazole-3,4-dicarboxylic acid diethyl ester (280 mg, 1.2 mmol) was suspended in a NaOH solution (0.5M in water, 2.8 ml) and stirred at r.t. until HPLC analysis indicated the consumption of the starting material (4 h). HCl (1N, 1 ml) was added, and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), evaporated, and the title compound (200 mg, 81%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=211.1 [M−H+].

Workup

  1. customthe consumption of the starting material (4 h)
  2. additionHCl (1N, 1 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-37874e8eaca74c7383ed501a4246bd2b
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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