HCID 58577742, Verbindung → N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine

HRID 587536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587536
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][C:19]([CH3:25])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C1COCC1.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([CH3:25])=[CH:18][N:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 58577742HCID 58577742, Verbindung

Produkt 1

HCID 58577457N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-[4-(benzyloxy)phenyl]-5-methyl-3-nitropyridin-2-amine (1.33 g) in acetic acid (10 mL) and THF (10 mL) was added zinc (2.59 g) at 0° C., and the mixture was stirred at 0° C. for 2 h. After stirring at room temperature overnight, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with AcOEt, washed with sat. NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 5%-50% AcOEt in hexane) to give N2-[4-(benzyloxy)phenyl]-5-methylpyridine-2,3-diamine (0.63 g) as a blue solid.

Aufarbeitung

  1. stirringAfter stirring at room temperature overnight
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with AcOEt
  5. washwashed with sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (NH silica gel, eluted with 5%-50% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ad65cac33ebc43c7ba761070bd324cea
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226921B2

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