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Potassium Permanganate → 3-Amino-6-chloro-4-methylpicolinic acid

HRID 887713
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887713
[NH2:1][C:2]1[C:3]([C:10]2[O:11]C=CC=2)=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].[Mn]([O-])(=O)(=O)=[O:16].[K+]>CC(C)=O.O>[NH2:1][C:2]1[C:3]([C:10]([OH:11])=[O:16])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 516875Potassium Permanganate2×HCID 593554283-Amino-6-chloro-2-(2-furanyl)-4-methylpyridine

Produkt 1

HCID 593553013-Amino-6-chloro-4-methylpicolinic acidAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Amino-6-chloro-2-(2-furanyl)-4-methylpyridine (400 mg) was dissolved in acetone (10 mL) and cooled in an ice bath to 0° C. A solution prepared of potassium permanganate (909 mg) in water (15 mL) was added drop wise to this solution. After complete addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was cooled again to 0° C. and a second portion of potassium permanganate (600 mg) in water (10 mL) was added and the cool bath removed. After stirring for 2 hours, the reaction mixture was filtered through a pad of celite, the filter cake was washed carefully with water, methanol and ethyl acetate and concentrated to approx. 10 mL on a rotary evaporator. 2N Sodium hydroxide solution was added to adjust the pH-value to −12 and the aqueous layer was washed 2× with MTB-ether. The aqueous layer was then adjusted to pH ˜2 by addition of 6N hydrochloric acid and extracted 3× with MTB-ether. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 262 mg of the title compound of the formula

Aufarbeitung

  1. additionwas added drop wise to this solution
  2. additionAfter complete addition
  3. temperatureto warm to room temperature
  4. temperatureThe mixture was cooled again to 0° C.
  5. customthe cool bath removed
  6. stirringAfter stirring for 2 hours
  7. filtrationthe reaction mixture was filtered through a pad of celite
  8. washthe filter cake was washed carefully with water, methanol and ethyl acetate
  9. concentrationconcentrated to approx. 10 mL on a rotary evaporator
  10. addition2N Sodium hydroxide solution was added
  11. washthe aqueous layer was washed 2× with MTB-ether
  12. additionThe aqueous layer was then adjusted to pH ˜2 by addition of 6N hydrochloric acid
  13. extractionextracted 3× with MTB-ether
  14. washThe combined organic layer was washed with brine
  15. dry with materialdried over MgSO4
  16. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a4ae83ddaa4a46468858989a860b4c92
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247431B2

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