O-Xylene → 2-Amino-4'-chlorobiphenyl

HRID 534710Notes

Reaction equation

HRID 534710 reaction equation
C1(C)C(C)=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)=[CH:12][CH:11]=1>[Pt].CC(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 7237O-XyleneHCID 2355494'-Chloro-2-nitro-1,1'-biphenyl

Product 1

HCID 2622612-Amino-4'-chlorobiphenyl

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

In a 20 ml autoclave were placed 1 g of xylene, 6 mg of a Pt/C catalyst (containing 1% by weight of Pt with respect to the weight of carbon) and 0.25 g (1 mmol) of 4′-chloro-2-nitrobiphenyl obtained in example 1.4. The mixture was stirred under hydrogen pressure (7-8 bar) at 100° C. until the starting material had disappeared (monitoring via HPLC). After completion of the reaction the mixture was cooled to ambient temperature and diluted with 15 ml of acetone. The catalyst was filtered off and the filtrate was evaporated in vacuo yielding 0.2 g (91% of theory) of the title compound in a purity of 93% (HPLC % by weight).

Workup

  1. customAfter completion of the reaction the mixture
  2. temperaturewas cooled to ambient temperature
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7edf882425b346a5b8725fcdced879a2
Source dataset
uspto-grants-2014_10
Patent number
US08853455B2

Reaction notes

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