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

HRID 1934312Notes

Reaction equation

HRID 1934312 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([N+:9]([O-])=O)[C:5]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)=[C:4]([F:23])[CH:3]=1>C(O)(=O)C.CO.[Fe]>[NH2:9][C:6]1[C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=[C:4]([F:23])[C:5]=1[C:12]1[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=1

Participants

5

Reactant 1

HCID 224661452-(4-Chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-3-chloro-5-trifluoromethylpyridine

Product 1

HCID 224661462-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-3-chloro-5-trifluoromethylpyridineYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

770 mg (13.7 mmol) of iron powder were added to 1.7 g (4.6 mmol) of 2-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-3-chloro-5-trifluoromethylpyridine in 9 ml of glacial acetic acid and 18 ml of methanol. The reaction mixture was refluxed for 15 hours with stirring and then concentrated under reduced pressure. The residue was taken up in 100 ml of ethyl acetate. Undissolved components were then filtered off. The filtrate was washed with 20 ml of water, dried over magnesium sulfate and finally concentrated. Yield: 96%; oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 hours
  2. concentrationconcentrated under reduced pressure
  3. filtrationUndissolved components were then filtered off
  4. washThe filtrate was washed with 20 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationfinally concentrated

Sources & evidence

ORD record
ord-fd09f87f2a1b4a6a9179d6741223f82d
Source dataset
uspto-grants-2002_05
Patent number
US06383986B1

Reaction notes

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