Water → 6-(Isobutylsulfonyl)picolinic acid

HRID 927785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927785
[CH2:1]([S:5]([C:8]1[N:13]=[C:12]([C:14]#N)[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3].[OH-:16].[Na+].[OH2:18]>>[CH2:1]([S:5]([C:8]1[N:13]=[C:12]([C:14]([OH:18])=[O:16])[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3]

Komponenten

4

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 710874716-(Isobutylsulfonyl)picolinonitrile

Produkt 1

HCID 710872496-(Isobutylsulfonyl)picolinic acidAusbeute 85 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of 6-(isobutylsulfonyl)picolinonitrile (126 mg, 562 μmol) and powdered sodium hydroxide (89.9 mg, 2.25 mmol) in water (15 mL) was heated to 90° C. for 24 h, poured into ice water/0.1 N aqueous HCl solution (1:1) and extracted 3 times with EtOAc. The organic layers were washed with ice water/brine (1:1), dried over Na2SO4 and concentrated in vacuo to give the title compound (116 mg, 85%) as white solid which was sufficiently pure to be used in the next reaction step. MS (EI): m/e=241.9 [M−H]−.

Aufarbeitung

  1. extractionextracted 3 times with EtOAc
  2. washThe organic layers were washed with ice water/brine (1:1)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6dd0ffe0dec94d28a468d36e276bb8a2
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290451B2

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