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 1271768Notes

Reaction equation

HRID 1271768 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-6493fc6b8ac6447f860334087ef23074
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Reaction notes

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