Cesium carbonate → N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine

HRID 82513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82513
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:12]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:25][CH:26]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 796132-Chloro-3-nitropyridineHCID 27238314-Benzyloxyaniline hydrochloride

Produkt 1

HCID 40676934N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-3-nitropyridine (2.0 g), 4-(benzyloxy)aniline hydrochloride (3.6 g), and cesium carbonate (12.3 g) in NMP (50 mL) was heated at 100° C. for 5 h. After cooling to rt, the mixture was partitioned between AcOEt and H2O. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (SiO2, hexane/AcOEt=1/1) to give N-[4-(benzyloxy)phenyl]-3-nitropyridin-2-amine (3.04 g) as a brown solid.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between AcOEt and H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, hexane/AcOEt=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-52bdcf4706404f93bb55fda81eab1280
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

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