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

HRID 586232Notes

Reaction equation

HRID 586232 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-9fa924521e6c4b3986a51cadf285f48a
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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