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

HRID 1192706Notes

Reaction equation

HRID 1192706 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([C:19](=[O:21])[CH3:20])[CH:3]=1.[H][H]>CO.[Pt]>[NH2:9][C:6]1[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([C:19](=[O:21])[CH3:20])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 866561861-(4-Chloro-3'-fluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 583684301-(6-Amino-4-chloro-3'-fluoro-5-methylbiphenyl-2-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-chloro-3′-fluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanone (4.43 g, 14.4 mmol) in 80 mL of methanol was hydrogenated in the presence of 443 mg of 5% Pt/C, under ballon pressure of hydrogen, overnight. After filtered off catalyst, the filtrate was concentrated under reduced pressure to give the desired product (4.00 g, 100%). LCMS calculated for C15H14ClFNO (M+H)+: m/z=278.1; Found: 278.1.

Workup

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

Sources & evidence

ORD record
ord-58adfffb1b1747358be04624c5e32e10
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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