Acetic Acid → 6-(Methanesulfonyl)pyridin-3-amine

HRID 1815107Notes

Reaction equation

HRID 1815107 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1)([O-])=O.C(O)(=O)C.C(OCC)(=O)C.CCCCCC.C(=O)(O)[O-].[Na+]>O.[Fe].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 12115522-(methylsulfonyl)-5-nitropyridineHCID 21226206Ethyl acetate hexane

Product 1

HCID 200389776-(Methanesulfonyl)pyridin-3-amineYield 70.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL). Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture. The mixture, which resulted, was heated to reflux for 2 hours. The reaction was monitored by thin layer chromatography (ethyl acetate/hexane, 1/1). The reaction mixture was then cooled to room temperature and a saturated solution of sodium bicarbonate (NaHCO3) (100 mL) was added to the mixture. Ethyl acetate (200 mL) was added to the above mixture and the mixture, which resulted, was stirred at room temperature for 30 minutes. The mixture was filtered through Celite® and the organic layer was collected. The aqueous layer was extracted with ethyl acetate (200 mL×3). The organic extractions were combined and dried over sodium sulfate. The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6 g, 70.5%).

Workup

  1. customThe mixture, which resulted
  2. temperaturewas heated
  3. temperatureto reflux for 2 hours
  4. customthe mixture, which resulted
  5. filtrationThe mixture was filtered through Celite®
  6. customthe organic layer was collected
  7. extractionThe aqueous layer was extracted with ethyl acetate (200 mL×3)
  8. extractionThe organic extractions
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-92c2c34b12e4413dadf02b0b69cb7757
Source dataset
uspto-grants-2005_04
Patent number
US06878726B2

Reaction notes

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