Hydrochloric Acid → 6-(Methylsulfanyl)pyridin-3-amine

HRID 1523272Notes

Reaction equation

HRID 1523272 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1.[OH-].[Na+]>[Fe].O>[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 44393132-(Methylthio)-5-nitropyridine

Product 1

HCID 102611796-(Methylsulfanyl)pyridin-3-amineYield 91.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron powder (3 g), water (20 mL) and concentrated hydrochloric acid (3 mL) were mixed, and 2-(methylthio)-5-nitropyridine (2 g, 12 mmol) was added portionwise. After reflux reaction for 2 hours, the reaction mixture was basified with 1N sodium hydroxide and extracted with 20 mL ethyl acetate for three times. The combined organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to yield the target compound (1.54 g, 11 mmol).

Workup

  1. temperatureAfter reflux
  2. customreaction for 2 hours
  3. extractionextracted with 20 mL ethyl acetate for three times
  4. dry with materialThe combined organic phase was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0de6d9c34ae445c68afc9dd16092e273
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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