Dimethylamine → N,N-dimethyl-5-nitropyridin-2-amine

HRID 450177

Reaktionsgleichung

Reaktionsgleichung von HRID 450177
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][NH:12][CH3:13]>CO>[CH3:11][N:12]([CH3:13])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 783082-Chloro-5-nitropyridine

Produkt 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 0.314 g (1.99 mmol) of 2-chloro-5-nitropyridine in MeOH (1 mL) was added 5 mL of dimethylamine (2M solution in MeOH) at 0° C. and the mixture was warmed to room temperature. The reaction mixture was concentrated and extracted with EtOAc. The organic layer was washed successively with sat. NaHCO3 solution and brine, dried (Na2SO4), and concentrated to give 0.313 g (94% yield) of 2-dimethylamino-5-nitropyridine as an orange powder: 1H NMR (CDCl3) δ9.06 (d, J=2.7 Hz, 1H), 8.20 (dd, J=9.5, 2.7 Hz, 1H), 6.46 (dd, J=9.5, 0.4 Hz, 1H), 3.23 (s, 6H); LCMS (APCI+) m/z: 168 (MH+, 100%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed successively with sat. NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-504f0d6541004dee8daa2c596cc37001
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486939B2

Verknüpfte Notizen

Wird geladen…