Stannous Chloride → 4-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine

HRID 1831540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831540
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=2[N+:22]([O-])=O)=[C:5]([CH3:25])[CH:4]=1.Cl[Sn]Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=2[NH2:22])=[C:5]([CH3:25])[CH:4]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 22052119[4-(4-Methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

Produkt 1

HCID 696581434-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

[4-(4-Methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine (0.43 g, 0.36 mmol) and SnCl2 (0.2 g, 1.08 mmol) in ethanol (2 mL) were heated to 70° C. for 4 h. The solution was cooled to room temperature and quenched with saturated aqueous NaHCO3 then extracted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a crude yield of 0.40 g (99%) of 4-(4-methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine; MS(EI) m/z 316.28 [(M+H)+, 100]. The crude product was taken on to Part E.

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. extractionthen extracted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5fcead9dbb9a40d99cee8441f4fc6cad
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067658B2

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