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

HRID 2121372Notes

Reaction equation

HRID 2121372 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) δ3.66 (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-d285909ab9cc489886c34cc4b0a27f90
Source dataset
uspto-grants-2004_02
Patent number
US06696444B2

Reaction notes

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