Sodium Hydroxide → 3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

HRID 1523578Notes

Reaction equation

HRID 1523578 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]#[N:24])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[OH-:25].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]([NH2:24])=[O:25])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67485570HCID 67485570, compound

Product 1

HCID 674861443-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (1.4 g, 4.19 mmol) was stirred in concentrated sulfuric acid (10 mL) overnight at ambient temperature. Ice (100 g) was added and the solution was neutralized using 4M NaOH. Ice was added as necessary to maintain the temperature below 20° C. The product was extracted into ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (1.5 g, 4.2 mmol).

Workup

  1. additionIce was added as necessary
  2. temperatureto maintain the temperature below 20° C
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d413ae4fd8b345f7b4e415be0108a923
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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