Methylamine → N2-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

HRID 533669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533669
N[C:2]1[C:3](Cl)=[N:4]C=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:13](CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26][NH2:27].[Cl-].[NH4+:29]>C(CC(=O)C)(=O)C.[Cu+2].CN1C(=O)CCC1>[CH3:26][NH:27][C:13]1[C:3]([NH2:4])=[CH:2][CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[N:29]=1

Komponenten

8

Edukt 5

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 31261AcetylacetoneHCID 129197572-Chloro-5-(trifluoromethyl)pyridin-3-amine

Produkt 1

HCID 68091056N2-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21863952acetylacetone copper(II)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a pressure-resistant reaction container, 3-amino-2-chloro-5-trifluoromethylpyridine (5 g), copper (II) acetylacetone (1.31 g), acetylacetone (2.50 g), cesium carbonate (16.25 g), NMP (20 ml), and 40% of aqueous methylamine solution (15 ml) were added, and stirred at 100° C. for 3 hours, at 120° C. for 3 hours, then at 140° C. for 5 hours. After the mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was poured thereinto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.09 g of N2-methyl-6-trifluoromethylpyridin-2,3-diamine.

Aufarbeitung

  1. waitat 140° C. for 5 hours
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d7e1ebc75d4a46fdbe5056a3cfaeaf67
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853238B2

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