Acetic Acid → 5-(Methylsulfanyl)pyridin-2-amine

HRID 1523266Notes

Reaction equation

HRID 1523266 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-])=O)=[N:7][CH:8]=1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Fe].O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 220361825-(Methylthio)-2-nitropyridine

Product 1

HCID 151797975-(Methylsulfanyl)pyridin-2-amineYield 83.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

5-(methylthio)-2-nitropyridine (270 g), iron powder (600 g), acetic acid (500 mL) and water (2 L) were heated to reflux for 4 hours. Then saturated sodium bicarbonate solution (6 L) was added into the reaction mixture. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic phase was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. After filtration, the residual solution was removed under reduced pressure to obtain the target compound (185 g). 1H-NMR (300 MHz, CDCl3): δ 2.39 (3H, s), 4.49 (2H, brs), 6.47 (1H, d), 7.50 (1H, dd), 8.11 (1H, d). LC-MS m/z: 141 [M++1].

Workup

  1. temperatureto reflux for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic phase was washed with saturated NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe residual solution was removed under reduced pressure

Sources & evidence

ORD record
ord-79b7c16ed00e4124addb64c975f3f45e
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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