Acetic Acid → 5-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

HRID 1022012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022012
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:6][N:5]=1)([O-:3])=[O:2].C=O.[C:18](O)(=O)C>CO>[CH3:18][N:13]1[CH2:12][CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[N:5][CH:6]=2)[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 866844372-Nitro-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridine

Produkt 1

HCID 580442465-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 232a (1.2 g, 5.8 mmol) in CH3OH (25 mL) was added HCHO (1 mL, 35 mmol) and acetic acid (1 mL), followed by the addition of NaBHCN3 (1.0 g, 12 mmol). The mixture was stirred at room temperature for 2 h. It was then evaporated under reduced pressure and the residue was purified by reverse-phase Combiflush eluting with 0.3% NH4HCO3 in water/acetonitrile to afford 232b as a yellow solid (1.0 g, 78%). MS-ESI: [M+H]+ 220.

Aufarbeitung

  1. additionfollowed by the addition of NaBHCN3 (1.0 g, 12 mmol)
  2. customIt was then evaporated under reduced pressure
  3. customthe residue was purified by reverse-phase Combiflush
  4. washeluting with 0.3% NH4HCO3 in water/acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-d38a7f35d18a4c04a0c9a6c023d75c40
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716274B2

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