Ammonium Chloride → 5-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one

HRID 2114892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114892
[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH3:13])[C:8](=[O:14])[CH2:7]2.[Cl-].[NH4+]>C(O)C.O.ClCCl.[Fe]>[NH2:15][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[N:9]([CH2:11][CH2:12][CH3:13])[C:8](=[O:14])[CH2:7]2

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 692726077-Fluoro-5-nitro-1-propyl-1,3-dihydro-indol-2-one

Produkt 1

HCID 692741315-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Iron powder (0.855 g, 15.3 mmol) is added in small portions to 7-fluoro-5-nitro-1-propyl-1,3-dihydro-indol-2-one (0.910 g, 3.82 mmol) and ammonium chloride (2.02 g, 38.2 mmol) in ethanol (60 ml) and water (30 ml) at 90° C. The reaction mixture is stirred vigorously and heated for 60 min, cooled to room temperature, and diluted with dichloromethane (300 ml). The mixture is filtered through celite, the organic layer separated and washed with water and brine, dried over sodium sulfate and evaporated to give the title compound as a dark brown solid. HPLC r.t. 3.03 min; MS for C11H13FN2O m/z 209.0 (M+H)+.

Aufarbeitung

  1. temperatureheated for 60 min
  2. filtrationThe mixture is filtered through celite
  3. customthe organic layer separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4d658204464b46289694d4adca22a817
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435751B2

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