4-Fluoro-2-nitroaniline → 2-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile

HRID 1350501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350501
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.F[C:13]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=1[C:15]#[N:16].O.[OH-].[Li+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=2[C:15]#[N:16])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 677694-Fluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 27745842-Fluoro-5-methylbenzonitrile

Produkt 1

HCID 210934602-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrileAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Combine 4-fluoro-2-nitro-phenylamine (2.9 g, 18.50 mmol), 2-fluoro-5-methyl-benzonitrile (2.5 g, 18.50 mmol) and lithium hydroxide monohydrate (2.4 g, 57.20 mmol) in methyl sulfoxide (DMSO, 40 ml). Heat the resulting mixture to 55° C. for 40 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Chromatograph the solid using flash chromatography and elute with mobile phase: 90% hexanes, 5% ethyl acetate, and 5% dichloromethane. Obtained 2.267 g of the title compound (8.36 mmol, 45% yield) as an orange amorphous solid.

Aufarbeitung

  1. temperatureCool the reaction mixture to ambient temperature
  2. filtrationFilter the resulting mixture
  3. customcollect the precipitate
  4. washelute with mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-398a6cb0d30d4a8789e95b1b4fdc2af6
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214673B2

Notizen zur Reaktion

Wird geladen…