5-Nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine → 6-[(2-Pyridinylmethyl)sulfanyl]-3-pyridineamine

HRID 856710Notes

Reaction equation

HRID 856710 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][CH:9]=1)([O-])=O>C(O)(=O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][S:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 695219185-Nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine

Product 1

HCID 433014876-[(2-Pyridinylmethyl)sulfanyl]-3-pyridineamineYield 34.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-nitro-2-[(2-pyridinylmethyl)sulfanyl]pyridine (6.0 g) was dissolved in acetic acid (60 ml), reduced iron (18 g) was added to the mixture, and the mixture was stirred for 240 hours at room temperature. The mixture was filtered with. Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 6-[(2-pyridinylmethyl)sulfanyl]-3-pyridineamine (1.83 g).

Workup

  1. filtrationThe mixture was filtered with
  2. washCelite, and washed 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-e38a987beda240139b158a0f4703e373
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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