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

HRID 2114880Notes

Reaction equation

HRID 2114880 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-])=O)=[CH:9][C:10]=2[F:12])[CH2:5][C:4]1=[O:16])[CH3:2].[Cl-].[NH4+]>C(O)C.O.ClCCl.[Fe]>[NH2:13][C:8]1[CH:7]=[C:6]2[C:11](=[C:10]([F:12])[CH:9]=1)[N:3]([CH2:1][CH3:2])[C:4](=[O:16])[CH2:5]2

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 692741011-Ethyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 692727925-Amino-1-ethyl-7-fluoro-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Iron powder (3.84 g, 68.7 mmol) is added in small portions to 1-ethyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one (3.85 g, 17.2 mmol) and ammonium chloride (8.94 g, 171 mmol) in ethanol (150 ml) and water (75 ml) at 90° C. The reaction mixture is stirred vigorously and heated for 30 min, cooled to room temperature, and diluted with dichloromethane (600 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 yellow solid. HPLC r.t. 2.60 min; MS for C10H11FN2O m/z 195.0 (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-a4806b725e124c7bb10ec67b41bb21c5
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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