2-(4-Chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-5-trifluoromethylpyridazin-3-one → 2-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-trifluoromethylpyridazin-3-one

HRID 277435Notes

Reaction equation

HRID 277435 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=[N:10]2)=[C:4]([N+:20]([O-])=O)[C:3]=1[OH:23]>C(O)(=O)C.[Fe]>[NH2:20][C:4]1[C:3]([OH:23])=[C:2]([Cl:1])[CH:7]=[C:6]([F:8])[C:5]=1[N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=[N:10]1

Participants

4

Reactant 1

HCID 186156602-(4-Chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-5-trifluoromethylpyridazin-3-one

Product 1

HCID 185196212-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-trifluoromethylpyridazin-3-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-5-trifluoromethylpyridazin-3-one (0.601 g) in acetic acid (6 ml) was added 0.38 g of iron powder at ambient temperature and stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography, eluted with hexane-ethyl acetate (2:1) to give 0.515 g of the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customAfter removing the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. washeluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-e55b008412ff49af87c7b44fd2f80562
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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