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

HRID 856712Notes

Reaction equation

HRID 856712 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:8][CH:9]=1)([O-])=O>C(O)(=O)C>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][S:10][C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:13]=1

Participants

3

Reactant 1

HCID 695227605-Nitro-2-[(3-pyridinylmethyl)sulfanyl]pyridine

Product 1

HCID 433014866-[(3-Pyridinylmethyl)sulfanyl]-3-pyridinylamineYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-nitro-2-[(3-pyridinylmethyl)sulfanyl]pyridine (5.6 g) was dissolved in acetic acid (56 ml), reduced iron (16.8 g) was added to the mixture, and the mixture was stirred for 40 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-[(3-pyridinylmethyl)sulfanyl]-3-pyridinylamine (4.3 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-3c677e70820f418cbffcd4464e115086
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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