2-[2-(2-Nitrophenyl)ethenyl]pyridine → 2-[2-(Pyridin-2-yl)ethyl]aniline

HRID 1659247Notes

Reaction equation

HRID 1659247 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 1427062-[2-(2-Nitrophenyl)ethenyl]pyridine

Product 1

HCID 47154222-[2-(Pyridin-2-yl)ethyl]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(o-nitrostyryl)pyridine (94.3 g., 0.42 mole) in 400 ml. of ethanol is reduced on a Parr hydrogenation apparatus employing 2 mg. of 10% palladium on carbon catalyst to provide 2-(o-aminophenethyl)pyridine, m.p. 59°-61° C. The isolation of the pyridine product is carried out in the usual manner by collecting the catalyst and evaporating the ethanolic solvent.

Sources & evidence

ORD record
ord-ba6eddcf601f46b59f351aa3063d50f7
Source dataset
uspto-grants-1981_12
Patent number
USRE030812

Reaction notes

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