1-(4-Chloro-3',5'-difluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanone → 1-(6-Amino-4-chloro-3',5'-difluoro-5-methylbiphenyl-2-yl)ethanone

HRID 1192709Notes

Reaction equation

HRID 1192709 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[C:5]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[C:4]([C:20](=[O:22])[CH3:21])[CH:3]=1.[H][H]>CO.[Pt]>[NH2:9][C:6]1[C:5]([C:12]2[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[CH:17]=2)=[C:4]([C:20](=[O:22])[CH3:21])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 866561871-(4-Chloro-3',5'-difluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 583685171-(6-Amino-4-chloro-3',5'-difluoro-5-methylbiphenyl-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-chloro-3′,5′-difluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanone (8.61 g 26.4 mmol) in 160 mL of methanol was hydrogenated in the presence of 0.86 of 5% Pt/C, under ballon pressure of hydrogen, overnight. After filtering off catalyst, the filtrate was concentrated under reduced pressure to give the desired product. LCMS calculated for C15H13ClF2NO (M+H)+: m/z=296.1; Found: 296.1.

Workup

  1. filtrationAfter filtering off catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-18fa23bdd80a41f3aebb8d154b5d0c3b
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…