2-nitro-4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-aniline → 4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine

HRID 1488960Notes

Reaction equation

HRID 1488960 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH:17]=[CH:16][C:15](=[O:18])[CH:14]=[CH:13]2)=[CH:7][C:5]=1[NH2:6])([O-])=O>CC(C)=O>[F:11][C:9]1[C:8]([N:12]2[CH:17]=[CH:16][C:15](=[O:18])[CH:14]=[CH:13]2)=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1

Participants

3

Reactant 1

HCID 229035842-nitro-4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-aniline

Product 1

HCID 229035734-fluoro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamineYield 85.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

First, 1.065 g of 2-nitro-4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-aniline was dissolved in 45 ml of dimethylformaldehyde by heating and reduced over 195 mg of 10% paradium-carbon catalyst under atmospheric pressure. After the reaction, the reaction mixture was filtered through celite to remove the catalyst, and the mother liquor thus obtained was concentrated to dryness. The residue thus obtained was subjected to column chromatography using 30 g of silica gel, and fractions eluted with a methylene chloride-methanol (20:1) solution were collected. The collected fractions were combined and evaporated. The residue was recrystallized with ethanol to give 802 mg of 4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine.

Workup

  1. temperatureby heating
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. customto remove the catalyst
  5. customthe mother liquor thus obtained
  6. concentrationwas concentrated to dryness
  7. customThe residue thus obtained
  8. washeluted with a methylene chloride-methanol (20:1) solution
  9. customwere collected
  10. customevaporated
  11. customThe residue was recrystallized with ethanol

Sources & evidence

ORD record
ord-d9be1dd908c1494caf0ce53a0360857b
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Reaction notes

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