Ammonium Chloride → HCID 69274126, compound

HRID 2114898Notes

Reaction equation

HRID 2114898 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-])=O)=[CH:10][C:11]=3[F:13])[CH2:6][C:5]2=[O:17])[CH2:3][CH2:2]1.[Cl-].[NH4+]>C(O)C.O.ClCCl.[Fe]>[NH2:14][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([F:13])[CH:10]=1)[N:4]([CH:1]1[CH2:2][CH2:3]1)[C:5](=[O:17])[CH2:6]2

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 692754101-Cyclopropyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

Product 1

HCID 69274126HCID 69274126, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Iron powder (0.994 g, 17.8 mmol) is added in small portions to 1-cyclopropyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one (1.05 g, 4.44 mmol) and ammonium chloride (2.32 g, 44.5 mmol) in ethanol (50 ml) and water (25 ml) at 90° C. The reaction mixture is stirred vigorously and heated for 60 min, cooled to room temperature, and diluted with dichloromethane (250 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 yellowish-brown solid. HPLC r.t. 2.62 min; MS for C11H11FN2O m/z 207.2 (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-e044301ff39f48fe99e0d6e529cb2e36
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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