2-[(4-Nitrophenyl)sulfanyl]pyridine → 4-[(Pyridin-2-yl)sulfanyl]aniline

HRID 856668Notes

Reaction equation

HRID 856668 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 40533372-[(4-Nitrophenyl)sulfanyl]pyridine

Product 1

HCID 189716604-[(Pyridin-2-yl)sulfanyl]anilineYield 90.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[(4-nitrophenylsulfanyl) pyridine (8.0 g) was dissolved in acetic acid (64 ml), and reduced iron (24 g) was added to the mixture, and then, the mixture was stirred for 16 hours at room temperature. The mixture was filtered with 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) aniline (6.3 g).

Workup

  1. filtrationThe mixture was filtered with 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-30c13dac58ac4403b9d81748d32546b9
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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