Ammonia → N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

HRID 533657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533657
[CH3:1][NH:2][C:3]1[C:8](Br)=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:27].[Cl-].[NH4+]>C(CC(=O)C)(=O)C.[Cu+2].CN1C(=O)CCC1>[CH3:1][NH:2][C:3]1[C:8]([NH2:27])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1

Komponenten

8

Edukt 5

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 31261AcetylacetoneHCID 679813233-bromo-N-methyl-5-(trifluoromethyl)pyridin-2-amine

Produkt 1

HCID 2735930N2-Methyl-5-(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, N-methyl-(3-bromo-5-trifluoromethyl-pyridin-2-yl)-amine (0.51 g), copper (II) acetylacetone (0.11 g), acetylacetone (0.20 g), cesium carbonate (1.30 g), NMP (2 ml), and 28% of aqueous ammonia (1 ml) were added, and stirred at 120° C. for 7 hours, then at 130° C. for 3 hours. The mixture was allowed to cool to room temperature, and then saturated aqueous ammonium chloride solution was poured, 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 0.28 g of N2-methyl-5-trifluoromethylpyridin-2,3-diamin.

Aufarbeitung

  1. waitat 130° C. for 3 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-73a9e64a3bdb4b72b34675b0f3862fdb
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853238B2

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