4-Nitroaniline → N-(4-Nitrophenyl)pyridin-2-amine

HRID 450064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450064
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[K+]>CS(C)=O.C(OCC)(=O)C.O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 74754-NitroanilineHCID 79732-BromopyridineHCID 14797Potassium Hydroxide

Produkt 1

HCID 12695755N-(4-Nitrophenyl)pyridin-2-amineAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-nitro aniline (2 g, 14.48 mmol) and 2-bromo pyridine (3.43 g, 21.72 mmol) in DMSO (12 ml) was added powdered potassium hydroxide (3.24 g, 57.92 mmol) at room temperature and the reaction mixture was heated at 100° C. for 15 hr. The reaction mixture was diluted with ethyl acetate, and water added. The organic layer was separated, washed with brine, dried and evaporated to give crude material. Purification by column chromatography using hexane/ethyl acetate (96:4) yielded (4-nitro-phenyl)-pyridin-2-yl-amine (0.28 g, 9%).

Aufarbeitung

  1. additionadded
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated
  6. customto give crude material
  7. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ddeb42bdee9b4d81b78cbedfac671330
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486962B2

Notizen zur Reaktion

Wird geladen…