Potassium Carbonate → 4-[(Pyridin-2-yl)sulfanyl]aniline

HRID 2222307Notes

Reaction equation

HRID 2222307 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)=O.CCOC(C)=O.O.[Fe]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 40533372-[(4-Nitrophenyl)sulfanyl]pyridine

Product 1

HCID 189716604-[(Pyridin-2-yl)sulfanyl]anilineYield 70.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-pyridinylthio)-1-nitrobenzene (Menai ST 3355A; 0.220 g, 0.95 mmol) and H2O (0.5 mL) in AcOH (5 mL) was added iron powder (0.317 g, 5.68 mmol) and the resulting slurry stirred for 16 h at room temp. The reaction mixture was diluted with EtOAc (75 mL) and H2O (50 mL), basified to pH 10 by adding solid K2CO3 in portions (Caution: foaming). The organic layer was washed with a saturated NaCl solution, dried (MgSO4), concentrated in vacuo. The residual solid was purified by MPLC (30% EtOAc/70% hexane) to give the desired product as a thick oil (0.135 g, 70%): TLC (30% EtOAc/70% hexanes) Rf 0.20. A3a. General Method for Substituted Aniline Formation Via Nitroarene Formation Through Nucleophilic Aromatic Substitution, Followed by Reduction

Workup

  1. washThe organic layer was washed with a saturated NaCl solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residual solid was purified by MPLC (30% EtOAc/70% hexane)

Sources & evidence

ORD record
ord-984913b06f6f4bf08cfd6d5a8b700bd0
Source dataset
uspto-grants-2008_05
Patent number
US07371763B2

Reaction notes

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