Ammonium Chloride → 3-Amino-6-fluoro-2-phenylaminobenzonitrile
Reaktionsgleichung
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.O.[Fe]>[NH2:17][C:5]1[C:6]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[C:8]#[N:9]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a mixture of 6-fluoro-3-nitro-2-phenylaminobenzonitrile (2.7 g, 10.5 mmol) in a mixture of MeOH (50 mL) and water (20 mL) were added NH4Cl (3.23 g, 62.9 mmol) and iron powder (2.3 g, 41.9 mmol) and the reaction mixture was heated at 90° C. for 1 h. After cooling to RT, the solid was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was partitioned between EtOAc and water and the aqueous phase was extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (930 mg, 39%). LCMS (Method B): RT 3.27 min [M+H]+ 227.8.
Aufarbeitung
- temperatureAfter cooling to RT
- filtrationthe solid was filtered through a pad of Celite®
- concentrationthe filtrate concentrated in vacuo
- customThe resulting residue was partitioned between EtOAc and water
- extractionthe aqueous phase was extracted with EtOAc (×3)
- washThe combined organic fractions were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-da7c8e982a454149b043004feefdfcf1
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08653089B2
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