4-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzonitrile → 4-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzylamine

HRID 1406330Notes

Reaction equation

HRID 1406330 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[F:15])=[C:4]([F:18])[CH:3]=1>N.[Ni]>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][C:8]=2[F:15])=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 1

HCID 667894214-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzonitrile

Product 1

HCID 584879074-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzylamineYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

1.0 g (3.76 mmol) of 4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzonitrile were hydrogenated in 30 mL methanolic ammonia solution with the addition of Raney nickel at 50° C. under a hydrogen pressure of 50 psi. Then the catalyst was filtered off and the filtrate was evaporated to dryness. The crude product thus obtained was reacted further without any further purification.

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-e937f86b4fdf4fd49a4a5821587aecaa
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

Loading…