Acetic Acid → 3-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

HRID 425910

Reaktionsgleichung

Reaktionsgleichung von HRID 425910
CC(O)=O.CCO.[Cl:8][C:9]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([Cl:27])[C:10]=1[CH2:11][O:12][C:13]1[C:14]([N+:19]([O-])=O)=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O.C(OCC)C>[Cl:8][C:9]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([Cl:27])[C:10]=1[CH2:11][O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 211113993-(2,6-Dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine

Produkt 1

HCID 211114003-(2,6-Dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared following procedure 1. To a stirred mixture of AcOH (650 mL) and EtOH (500 mL) was suspended 3-(2,6-dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine (9.43 g, 0.028 mol) and iron chips (15.7 g, 0.28 mol). The reaction was heated slowly to reflux and allowed to stir for 1 hr. The reaction was cooled to room temperature then diethyl ether (500 mL) and water (500 mL) was added. The solution was carefully neutralized by the addition of sodium carbonate. The combined organic extracts were washed with sat'd NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL) then dried (Na2SO4), filtered and concentrated to dryness under vacuum to yield 3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (9.04 g, 0.027 mol, 99%) as a light pink solid. 1H NMR (CDCl3, 300 MHz) δ 1.8-1.85 (d, 3H), 4.9-5.2 (brs, 2H), 6.7-6.84 (q, 1H), 7.0-7.1 (m, 1H), 7.2-7.3 (m, 1H), 7.6-7.7 (m, 1H).

Aufarbeitung

  1. custom3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared
  2. temperatureThe reaction was heated slowly
  3. temperatureto reflux
  4. washThe combined organic extracts were washed with sat'd NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL)
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a79387d940143c6962fe47f4b2e114b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106197B2

Verknüpfte Notizen

Wird geladen…