Water → HCID 58577742, Verbindung

HRID 82617

Reaktionsgleichung

Reaktionsgleichung von HRID 82617
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([CH3:27])=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([CH3:27])=[CH:20][N:19]=2)=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8183002-Chloro-5-methyl-3-nitropyridineHCID 27238314-Benzyloxyaniline hydrochloride

Produkt 1

HCID 58577742HCID 58577742, VerbindungAusbeute 22,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-(benzyloxy)aniline hydrochloride (4.10 g) and 2-chloro-5-methyl-3-nitropyridine (3.0 g) in DMF (30 mL) was added TEA (7.27 mL) at room temperature, and the mixture was stirred at room temperature for 2 h. The mixture was heated to 60° C. After stirring at 60° C. overnight, K2CO3 (4.81 g) was added to the mixture. The mixture was heated to 100° C. and stirred at 100° C. overnight. The mixture was poured into water and the mixture was extracted with AcOEt. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-30% AcOEt in hexane) to give N-[4-(benzyloxy)phenyl]-5-methyl-3-nitropyridin-2-amine (1.33 g) as a red solid.

Aufarbeitung

  1. temperatureThe mixture was heated to 60° C
  2. stirringAfter stirring at 60° C. overnight
  3. temperatureThe mixture was heated to 100° C.
  4. stirringstirred at 100° C. overnight
  5. extractionthe mixture was extracted with AcOEt
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-30% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d89d58304d3c4849b30f48ebd5331560
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

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