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

HRID 929919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929919
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d236a53bbc18460e902edc237568ac13
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296725B2

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