2-[(4-nitrophenyl)methylsulfanyl]pyridine → 4-[(Pyridin-2-ylsulfanyl)methyl]aniline

HRID 856666Notes

Reaction equation

HRID 856666 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:9][CH2:8][C:7]1[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 6770632-[(4-nitrophenyl)methylsulfanyl]pyridine

Product 1

HCID 284023404-[(Pyridin-2-ylsulfanyl)methyl]anilineYield 38.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[(4-nitrobenzyl)sulfanyl]pyridine (14.5 g) was dissolved in acetic acid (145 ml), reduced iron (43.5 g) was added to the solution, and then, the mixture was stirred for 20 hours at room temperature. The mixture was filtered by Celite, washed with ethyl acetate, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[(2-pyridinylsulfanyl)methyl]aniline (4.9 g).

Workup

  1. filtrationThe mixture was filtered by Celite
  2. washwashed with ethyl acetate
  3. customthe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f72d715f7a64c03ac5566aea0820715
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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