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

HRID 1516301Notes

Reaction equation

HRID 1516301 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-e2f290278f194285af8251ece4f423c4
Source dataset
uspto-grants-2012_07
Patent number
US08227475B2

Reaction notes

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