HCID 10750450, compound → HCID 18973056, compound

HRID 2394334Notes

Reaction equation

HRID 2394334 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]#[N:10])[C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1>C(O)C.[Ni].O>[NH2:11][C:5]1[C:6]([CH2:8][C:9]#[N:10])=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 1

HCID 10750450HCID 10750450, compound

Product 1

HCID 18973056HCID 18973056, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of (2-chloro-5-nitro-4-pyridyl) acetonitrile in ethanol (100 mL) was added to a suspension of 50% Raney nickel in water (3.2 g) diluted with ethanol (150 mL). The mixture was hydrogenated in a Parr shaker at 3 atmospheres pressure for 2.5 hours and then filtered through Celite® (diatomaceous earth) to remove the catalyst. The solvent was removed in vacuo to leave a dark oil which was subjected to flash chromatography on silica gel using 3:1 ethyl acetate/hexanes as eluant. Fractions containing only the title compound were combined and concentrated to afford an oil (850 mg, 32%). Less pure fractions were also combined and concentrated to give an oil (600 mg) of which the title compound was the major component (about 75%).

Workup

  1. filtrationfiltered through Celite® (diatomaceous earth)
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuo
  4. customto leave a dark oil which

Sources & evidence

ORD record
ord-18b002708c674c9681245a2694f1d702
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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