Sodium Hydroxide → HCID 86634792, compound

HRID 911091Notes

Reaction equation

HRID 911091 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[C:11]([CH2:16][OH:17])[CH:12]=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].[O-:21][Mn](=O)(=O)=O.[K+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([CH3:15])=[N:13][CH:12]=[C:11]([C:10]=2[CH3:18])[C:16]([OH:21])=[O:17])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 86634791(5-(2-Chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol

Product 1

HCID 86634792HCID 86634792, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-(2-chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol (5.00 g, 18.9 mmol) was charged with NaOH (0.1N in H2O, 19 ml, 1.9 mmol). 3% Aqueous KMnO4 (119 ml, 22.7 mmol) was then added. The reaction stirred at room temperature overnight. The solution was diluted with dichloromethane, filtered through celite, and acidified with citric acid. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layers were dried and concentrated to give 5-(2-chloropyridin-4-yloxy)-4,6-dimethylnicotinic acid (2.66 g, 51%).

Workup

  1. filtrationfiltered through celite
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM
  4. customThe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-04e0f57cc4c6498eab32c586091849e5
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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