Ammonium Chloride → 5-Amino-7-fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one

HRID 2114887Notes

Reaction equation

HRID 2114887 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][F: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][F:13])[C:8](=[O:14])[CH2:7]2

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 739475807-Fluoro-1-(2-fluoro-ethyl)-5-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 739475815-Amino-7-fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Iron powder (0.416 g, 7.43 mmol) is added in small portions to 7-fluoro-1-(2-fluoro-ethyl)-5-nitro-1,3-dihydro-indol-2-one (Step 3, 0.45 g, 1.86 mmol) and ammonium chloride (0.987 g, 18.6 mmol) in ethanol (40 ml) and water (20 ml) at 90° C. The reaction mixture is stirred vigorously and heated for 30 min, cooled to room temperature, and diluted with dichloromethane (100 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. 2.34 min; MS for C10H10F2N2O m/z 213.2 (M+H)+.

Workup

  1. temperatureheated for 30 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-5d0b8bf8f933456dae89ed260a0e9ab8
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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