Acetic Acid → N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

HRID 572187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572187
C(O)(=O)C.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([N+:26]([O-])=O)=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.[Zn]>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 58577297N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine

Produkt 1

HCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of zinc (40.2 g), THF (50 ml) and acetic acid (100 ml) was added slowly a solution of N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine (13.75 g) in THF (150 ml), and the obtained mixture was stirred at room temperature for 30 min. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (8.77 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 1 M aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5255e91a25ce4e91b1675ac650228100
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029388B2

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