Ethanol → 3-Benzoylamino-5-chloro-2-pyridone

HRID 259549Notes

Reaction equation

HRID 259549 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5](=[O:8])[NH:6][CH:7]=1.[CH2:12]([OH:14])[CH3:13]>[Pd].C(O)(=O)C>[C:12]([NH:9][C:4]1[C:5](=[O:8])[NH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:14])[C:13]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 2480485-Chloro-2-hydroxy-3-nitropyridine

Product 1

HCID 227548073-Benzoylamino-5-chloro-2-pyridone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5-Chloro-3-nitro-2-pyridone (5.3 g.) was hydrogenated in 225 ml. of ethanol and 6 ml. of acetic acid in the presence of 0.6 g. of 5% palladium-on-carbon. The catalyst was removed by filtration and the filtrate was concentrated to dryness. The residue was dissolved in 75 ml. of pyridine, cooled in ice and treated over 15 minutes with 4.8 g. of benzoyl chloride. The ice bath and reaction mixture were allowed to warm to room temperature spontaneously. The mixture was poured onto 200 g. of ice. On dilution with 500 ml. of water an oil separated which on washing with water solidified (4 g.). The crude 3-benzoylamino-5-chloro-2-pyridone was used directly in the next step.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe residue was dissolved in 75 ml
  4. temperatureof pyridine, cooled in ice
  5. additiontreated over 15 minutes with 4.8 g
  6. customThe ice bath and reaction mixture
  7. additionThe mixture was poured onto 200 g
  8. customof water an oil separated which
  9. washon washing with water

Sources & evidence

ORD record
ord-92d92970ba9e4654888bb3e2a6a8e962
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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