3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine → 3-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine

HRID 1426166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426166
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-])=O)=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.ClCCl.[Zn]>[CH2:1]([O:8][C:9]1[C:10]([NH2:23])=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 673694033-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

Produkt 1

HCID 673705813-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amineAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Zinc (1.34 g, 20.5 mmol) was added slowly to a solution of 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.730 g, 2.05 mmol) in acetic acid (20 mL) in a water bath. The reaction mixture was stirred 2 hours, then diluted with dichloromethane (100 mL) and filtered through Celite. The pad was washed several times with dichloromethane, and the combined filtrates were concentrated. The residue was partitioned between ethyl acetate and 2N NaOH, and the organic layer was washed with brine, dried, and concentrated to afford 3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine (0.66 g, 98.7% yield) as a light yellow oil. 1H NMR (CDCl3) δ 4.85 (bs, 2H), 5.03 (s, 2H), 6.79-6.83 (m, 2H), 7.02 (t, 1H), 7.14 (t, 1H), 7.37-7.47 (m, 7H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. washThe pad was washed several times with dichloromethane
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was partitioned between ethyl acetate and 2N NaOH
  5. washthe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1656dbb393d24203a6b5c7cd91069b6a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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