Bromoacetic Acid → 2-(4-nitro-1H-pyrazol-1-yl)acetic acid

HRID 929919Notes

Reaction equation

HRID 929919 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)([O-:5])=[O:4].Br[CH2:12][C:13]([OH:15])=[O:14]>O.CC(C)=O>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:12][C:13]([OH:15])=[O:14])[CH:10]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 163764-nitro-1H-pyrazole

Product 1

HCID 12834772-(4-nitro-1H-pyrazol-1-yl)acetic acidYield 88%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (32.7 g, 0.58 mol) in water (100 mL) was added to a stirred mixture of 4-nitro-1H-pyrazole (30 g, 0.27 mol) in acetone (500 mL) at room temperature. After 30 min, a solution of 2-bromoacetic acid (38.7 g, 0.27 mol) in acetone (100 mL) was added and the reaction was stirred overnight. The solvent was removed in vacuo, the residue was diluted with water then extracted three times with ethyl acetate and the combined organic layer was concentrated in vacuo. The residue was further extracted with dichloromethane and methanol and the combined organic layer was concentrated in vacuo to afford 2-(4-nitro-1H-pyrazol-1-yl)acetic acid (40 g, 88%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionthen extracted three times with ethyl acetate
  4. concentrationthe combined organic layer was concentrated in vacuo
  5. extractionThe residue was further extracted with dichloromethane and methanol
  6. concentrationthe combined organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-d236a53bbc18460e902edc237568ac13
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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