Pyridine → 2-(4-Fluorophenyl)-5-cyanopyridine

HRID 1788643Notes

Reaction equation

HRID 1788643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10](Cl)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 27737342-Chloro-6-(4-Fluorophenyl)Nicotinonitrile

Product 1

HCID 139315862-(4-Fluorophenyl)-5-cyanopyridineYield 51.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Fluorophenyl)-5-cyano-6-chloropyridine (8.6 g) prepared in Example 1 was dissolved in ethyl acetate (300 ml), followed by adding to the solution, Pd-C (1 g) and triethylamine (12 ml), subjecting the above pyridine derivative to catalytic reduction at ordinary temperature and ordinary pressure, thereafter adding water (100 ml), filtering, withdrawing the ethyl acetate layer separated from the filtrate, twice washing it with water, distilling off ethyl acetate, and recrystallizing the residue from ethanol to obtain the objective 2-(4-fluorophenyl)-5-cyanopyridine (3.8 g). M.P.: 149.0° C.

Workup

  1. filtrationadding water (100 ml), filtering
  2. customwithdrawing the ethyl acetate layer
  3. customseparated from the filtrate
  4. washtwice washing it with water
  5. distillationdistilling off ethyl acetate
  6. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-208c234460af47f4a565f140bd3ccc36
Source dataset
uspto-grants-1987_08
Patent number
US04684477

Reaction notes

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