2-Amino-3-nitro-6-(phenylmercapto)pyridine → 2,3-Diamino-6-(phenylmercapto)pyridine

HRID 23928Notes

Reaction equation

HRID 23928 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[H][H]>CC(O)C.[Ni]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

5

Reactant 2

HCID 110212152-Amino-3-nitro-6-(phenylmercapto)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 110638822,3-Diamino-6-(phenylmercapto)pyridineYield 87.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

2,3-Diamino-6-(phenylmercapto)pyridine was prepared by hydrogenating 2-amino-3-nitro-6-(phenylmercapto)pyridine (107.1 g, 0.433 mol) under 5 atm of H2 in the presence of 30 g of Raney-Ni in 1200 mL of 2-propanol at 70° C. After 4 hours (29.1 L of hydrogen) the reaction mixture was cooled to 4° C. while stirring continuously. The precipitate was collected by vacuum filtration, washed with 2-propanol and dried at 50° C. under vacuum. The combined filtrates were concentrated under reduced pressure and recrystallized from 2-propanol. After washing the hydrogenation apparatus twice with 1000 mL of THF, evaporation under reduced pressure and recrystallization from 2-propanol, the precipitate was collected and dried at 50° C. under vacuum to give 80.4 g (87.1% yield) of 2,3-diamino-6-(phenylmercapto)pyridine, m.p. 119-122° C.).

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with 2-propanol
  3. customdried at 50° C. under vacuum
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customrecrystallized from 2-propanol
  6. washAfter washing the hydrogenation apparatus
  7. customtwice with 1000 mL of THF, evaporation
  8. customunder reduced pressure and recrystallization from 2-propanol
  9. customthe precipitate was collected
  10. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-e7470fec11ee4480a0d39df923659c49
Source dataset
uspto-grants-2005_02
Patent number
US06855723B2

Reaction notes

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