Ammonium Chloride → HCID 11951851, compound

HRID 2114875Notes

Reaction equation

HRID 2114875 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]([CH:11]([CH3:13])[CH3:12])[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]([CH:11]([CH3:12])[CH3:13])[C:8](=[O:14])[CH2:7]2

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 119518507-Fluoro-1-isopropyl-5-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 11951851HCID 11951851, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Iron powder (0.854 g, 15.3 mmol) is added portionwise to a mixture of 7-fluoro-1-isopropyl-5-nitro-1,3-dihydro-indol-2-one (17, 0.91 g, 3.82 mmol) and ammonium chloride (2.04 g, 38.2 mmol) in ethanol (50 ml) and water (25 ml) at 90° C. The reaction is stirred vigorously and heated for 30 min, cooled to room temperature and diluted with dichloromethane (150 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 solid. HPLC r.t. 2.97 min; MS for C11H13FN2O m/z 209.1 (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-4b820921d2a84acf87758029448e138f
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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