Nicotinamide → 3-Amino-2-chloro-6-methyl-4-(trifluoromethyl)pyridine

HRID 53514

Reaktionsgleichung

Reaktionsgleichung von HRID 53514
[OH-].[Na+].BrBr.NC([C:8]1[C:9]([Cl:19])=[N:10][C:11]([CH3:18])=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15])=O.[NH2:20]C(C1C=NC=CC=1)=O>O>[NH2:20][C:8]1[C:9]([Cl:19])=[N:10][C:11]([CH3:18])=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15]

Komponenten

6

Edukt 4

HCID 936NicotinamideHCID 14798Sodium HydroxideHCID 24408BromineHCID 199600523-Aminocarbonyl-2-chloro-6-methyl-4-(trifluoromethyl)pyridine

Produkt 1

HCID 199600793-Amino-2-chloro-6-methyl-4-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 6.6 g of sodium hydroxide in 60 ml of water at 5° C. was added 9.3 g of bromine. When a clear solution was obtained, 9.2 g of 3-aminocarbonyl-2-chloro-6-methyl-4-(trifluoromethyl)pyridine was added quickly, maintaining the temperature below 5° C. The resulting mixture was stirred until the 3-(aminocarbonyl)pyridine dissolved (~30 min). The cooling bath was removed and the mixture was then warmed to 75° C. for 30 min. After cooling to room temperature, the 3-aminopyridine product was extracted with ethyl acetate, dried (magnesium sulfate), filtered, and evaporated to give 4.9 g of the desired product.

Aufarbeitung

  1. customWhen a clear solution was obtained
  2. temperaturemaintaining the temperature below 5° C
  3. dissolutiondissolved (~30 min)
  4. customThe cooling bath was removed
  5. temperatureAfter cooling to room temperature
  6. extractionthe 3-aminopyridine product was extracted with ethyl acetate
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d1e9210922024c1794abea3aecf6bd64
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620974

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