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

HRID 2114892Notes

Reaction equation

HRID 2114892 reaction equation
[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-4d658204464b46289694d4adca22a817
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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