Dimethylformamide → 6-(Cyclopentyloxy)pyridin-3-amine

HRID 1294829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294829
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[N:8][CH:9]=1)([O-])=O.Br[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:12]1([O:10][C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178526703HCID 178526703, Verbindung

Produkt 1

HCID 167909726-(Cyclopentyloxy)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-nitropyridin-2-ol (14.0 g), bromocyclopentane (8.0 g), potassium carbonate (14 g) and DMF (200 mL) was heated at 80° C. for 6 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The resulting product (2-cyclopentyloxy-5-nitropyridine) was hydrogenated in ethanol using palladium(II) hydroxide as catalyst. The product with the molecular weight of 178.24 (C10H14N20) was obtained in this way; MS (ESI): 179 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product with the molecular weight of 178.24 (C10H14N20) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-dd01796d942645b594afdabc12631e92
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241787B2

Notizen zur Reaktion

Wird geladen…