4,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile → 5'-Amino-4,2'-difluorobiphenyl-2-carbonitrile

HRID 1167121Notes

Reaction equation

HRID 1167121 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[F:17])=[CH:6][CH:7]=1>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]([F:17])=[C:8]([C:5]2[C:4]([C:18]#[N:19])=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:13]=1

Participants

5

Reactant 1

HCID 112424114,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

Product 1

HCID 112647035'-Amino-4,2'-difluorobiphenyl-2-carbonitrileYield 100%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4,2′-difluoro-5′-nitrobiphenyl-2-carbonitrile (26 g, 100 mmol) in ethanol (180 ml) and ethyl acetate (180 ml) was treated with platinum(IV) oxide (1.02 g, 4.5 mmol) and then shaken under an atmosphere of hydrogen (40 psi) for 1 h. [The reaction was very exothermic and complete solution is brought about by the increase in temperature]. The catalyst was removed by filtration through glass microfibre filter paper [if any crystalline product is present the filter cake is washed with dichloromethane] and the filtrate evaporated to dryness to afford 5′-amino-4,2′-difluorobiphenyl-2-carbonitrile as a straw-coloured solid (23 g, 100%): 1H NMR (360 MHz, CDCl3) δ 3.66 (2H, s), 6.66-6.70 (1H, m), 6.71-6.74 (1H, m), 7.00 (1H, dd, J 9, 9 Hz), 7.33-7.38 (1H, m), 7.44-7.49 (1H, m).

Workup

  1. temperatureincrease in temperature]
  2. customThe catalyst was removed by filtration through glass microfibre
  3. filtrationfilter paper [if any crystalline product
  4. washis washed with dichloromethane] and the filtrate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-85b77720b3fb4174a2d838d356b5e04b
Source dataset
uspto-grants-2003_09
Patent number
US06617326B2

Reaction notes

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