1-(4-Nitro-phenyl)-1H-pyridin-4-one → 1-(4-Amino-phenyl)-1H-pyridin-4-one

HRID 18531Notes

Reaction equation

HRID 18531 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[CH:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:11]=[CH:12][C:13](=[O:16])[CH:14]=[CH:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 197886281-(4-Nitro-phenyl)-1H-pyridin-4-one

Product 1

HCID 574375331-(4-Amino-phenyl)-1H-pyridin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 g 1-(4-Nitro-phenyl)-1H-pyridin-4-one in 510 mL ethyl acetate and 26 mL ethanol, 52.1 g SnCl2 dihydrate were added and the reaction mixture was heated to reflux for 6 h. Then, after cooling to RT the solvents were removed under reduced pressure. The residue was taken-up in 100 mL aqueous NaHCO3 solution and 200 mL ethyl acetate were added. The inorganic precipitate was filtered off and the solids were washed with ethyl acetate. After separation of the organic layer, the aqueous layer of the filtrate was extracted with ethyl acetate (2×100 ml) and with DCM (3×150 ml). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure. The remaining product was pure enough for the next reaction step. Yield: 6 g.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customwere removed under reduced pressure
  4. addition200 mL ethyl acetate were added
  5. filtrationThe inorganic precipitate was filtered off
  6. washthe solids were washed with ethyl acetate
  7. customAfter separation of the organic layer
  8. extractionthe aqueous layer of the filtrate was extracted with ethyl acetate (2×100 ml) and with DCM (3×150 ml)
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. customthe solvents were removed under reduced pressure
  11. customThe remaining product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-adfdfa5cf8f54119aa7584a5598c94b4
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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