Ethyl Acetate → HCID 67320692, compound

HRID 1967003Notes

Reaction equation

HRID 1967003 reaction equation
[Cl:1][C:2]1[C:3]([F:16])=[CH:4][C:5]([N+:13]([O-])=O)=[C:6]([N:8]([CH:10]2[CH2:12][CH2:11]2)[CH3:9])[CH:7]=1.C(OCC)(=O)C>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH:10]2[CH2:11][CH2:12]2)[CH3:9])[C:5]([NH2:13])=[CH:4][C:3]=1[F:16]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67320191HCID 67320191, compound

Product 1

HCID 67320692HCID 67320692, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 400 mg (16.35 mmol) (5-chloro-4-fluoro-2-nitro-phenyl)-cyclopropyl-methyl-amine in 4 mL methanol was added 40 mg 10% palladium on activated charcoal (Fluka). The reaction mixture was stirred at room temperature under a hydrogen atmosphere of 1.7 bar for two hours. Ethyl acetate (10 mL) was added and the reaction mixture was filtered over Dicalite® speed plus (Acros) and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40) to give 240 mg (68%) of the title compound as a brown liquid. MS (ESI): m/z=215.075 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered over Dicalite® speed plus (Acros)
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record
ord-1e917e8f5c174c4e93e141abffdff2e3
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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