Hydrochloric Acid → 6-Methyl-4-(pyrimidin-5-yloxy)picolinic acid

HRID 1525839Notes

Reaction equation

HRID 1525839 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#N)[CH:5]=[C:4]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:3]=1.[OH-:17].[Na+].Cl.[O:20]1CCOCC1>CO.C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:20])=[O:17])[CH:5]=[C:4]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 682949096-Methyl-4-(pyrimidin-5-yloxy)picolinonitrile

Product 1

HCID 682948266-Methyl-4-(pyrimidin-5-yloxy)picolinic acidYield 99%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-methyl-4-(pyrimidin-5-yloxy)picolinonitrile (4.31 g, 20.3 mmol, 1.00 eq) was dissolved in dioxane (90 mL), and 2N NaOH (45 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 2N HCl (45 mL). The water and solvent were removed in vacuo and the crude reaction was dissolved in 10% MeOH/CH2Cl2. The undissolved salt was filtered off and the solvents were removed in vacuo to afford 4.65 g (99%) of the title compound as a white solid which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureafter cooling the reaction
  3. customThe water and solvent were removed in vacuo
  4. customthe crude reaction
  5. filtrationThe undissolved salt was filtered off
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-03afd64567f841908b244f3e334bfa58
Source dataset
uspto-grants-2015_07
Patent number
US09085562B2

Reaction notes

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