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

HRID 1525839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525839
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-03afd64567f841908b244f3e334bfa58
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085562B2

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