Potassium Hydroxide → 3-(methoxycarbonyl)-1-(2-ethoxyethyl)-4-nitro-1H-pyrazole-5-carboxylic acid

HRID 2401301Notes

Reaction equation

HRID 2401301 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]([O:13]C)=[O:12])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]([C:18]([O:20][CH3:21])=[O:19])=[N:7]1)[CH3:2].[OH-].[K+]>CO>[CH3:21][O:20][C:18]([C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[C:10]([C:11]([OH:13])=[O:12])[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[N:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57446145Dimethyl 1-(2-ethoxyethyl)-4-nitro-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 534394903-(methoxycarbonyl)-1-(2-ethoxyethyl)-4-nitro-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of step 1 (1.63 g, 5.4 mmol) was added to a solution of potassium hydroxide (330 mg, 5.9 mmol) in methanol (20 mL) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the crude product dissolved in water and washed with ether. The aqueous phase was acidified with 2M hydrochloric acid and extracted into dichloromethane (3×100 mL). The organics were combined, dried over magnesium sulphate and concentrated in vacuo to yield the nitro product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe crude product dissolved in water
  3. washwashed with ether
  4. extractionextracted into dichloromethane (3×100 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a47ae7133d37460cad4e75224b45a3d8
Source dataset
uspto-grants-2014_08
Patent number
US08796287B2

Reaction notes

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