Ammonia → 1-[4-(4-Chloro-2-fluoro-phenoxy)-phenyl]-ethylamine

HRID 1406333Notes

Reaction equation

HRID 1406333 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](=[N:15]O)[CH3:14])=[CH:9][CH:8]=2)=[C:4]([F:19])[CH:3]=1.N.[H][H]>CO.[Ni]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]([NH2:15])[CH3:14])=[CH:11][CH:12]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 866588121-[4-(4-Chloro-2-fluoro-phenoxy)-phenyl]-ethanone-oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 584879121-[4-(4-Chloro-2-fluoro-phenoxy)-phenyl]-ethylamineYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2.60 g (9.3 mmol) of 1-[4-(4-chloro-2-fluoro-phenoxy)-phenyl]-ethanone-oxime were dissolved in 20 mL methanol, then combined with 30 mL 7N methanolic ammonia solution and after the addition of 0.2 g Raney nickel hydrogenated at ambient temperature and 50 psi hydrogen pressure. Then the catalyst was filtered off and the filtrate was evaporated down. The crude product thus obtained was reacted further without any further purification.

Workup

  1. customhydrogenated at ambient temperature
  2. filtrationThen the catalyst was filtered off
  3. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-3d8902e9953a4ddfa68ff2712a45a7f9
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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