3-[(4-Nitrophenyl)methyl]pyridine → 4-(Pyridin-3-ylmethyl)aniline

HRID 2413057Notes

Reaction equation

HRID 2413057 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 133648603-[(4-Nitrophenyl)methyl]pyridineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 103751334-(Pyridin-3-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(4'-nitrobenzyl)pyridine of Preparation 8 (7.924 g, 0.0370 mole) in methanol (100 ml) is shaken with 5% Pd on carbon and hydrogen in a Parr apparatus. Hydrogen uptake is complete within 45 min. The catalyst is removed by filtration through sintered glass. The solvent is removed under reduced pressure. The crystalline residue is recrystallized from methylene chloride-hexane with a first crop of 5.229 g; a second crop of 0.492 g; a third crop of 0.480 g; and a fourth crop of 0.137 g (total 6.338 g, 0.0347 mole, 94%). Recrystallization from CH2Cl2 -hexane gives colorless crystals of the titled product with a melting point of 121°-123° C.; IR (nujol) peaks are observed at 3400, 3300, 3200, 1640, 1610, 1590, 1575, 1515, 1480, 845, 800, and 710 cm-1.

Workup

  1. customThe catalyst is removed by filtration through sintered glass
  2. customThe solvent is removed under reduced pressure
  3. customThe crystalline residue is recrystallized from methylene chloride-hexane with a first crop of 5.229 g
  4. customRecrystallization from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-b47dd4c053cf4380a1dd1565e9090f5b
Source dataset
uspto-grants-1985_01
Patent number
US04495357

Reaction notes

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