Water → 6-(Isobutylsulfonyl)picolinic acid

HRID 632399Notes

Reaction equation

HRID 632399 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 710872496-(Isobutylsulfonyl)picolinic acidYield 85%

Conditions

Temperature
90 °C

Procedure

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]−.

Workup

  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

Sources & evidence

ORD record
ord-8d21d0c342e64dcf858e44ddb5f1fdcf
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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