4-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-2-nitrobenzenol → 2-Amino-4-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]benzenol

HRID 1276074Notes

Reaction equation

HRID 1276074 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([N+:19]([O-])=O)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1>CO.C(O)(=O)C.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([NH2:19])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 1

HCID 1355499694-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-2-nitrobenzenol

Product 1

HCID 1355499702-Amino-4-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]benzenol

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.2 g (110 mmol) of iron powder were heated to reflux temperature in a mixture of 66 ml of methanol and 33 ml of glacial acetic acid and treated in portions with a total of 11.7 g (36.7 mmol) of 3-chloro-2-(4-hydroxy-3-nitrophenyl)-5-trifluoromethylpyridine. After addition was complete. The mixture was heated for a further 2 hours at reflux temperature, allowed to cool and diluted with 130 ml of ethyl acetate. The solid components were separted off, washed with ethyl acetate and discarded. The filtrate was treated with water so that two phases were formed. The aqueous phase was separated off and extracted twice with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and filtered through silica gel. Yield: 7.8 g (74%) of a dark oil.

Workup

  1. temperatureto reflux temperature
  2. additionAfter addition
  3. temperatureThe mixture was heated for a further 2 hours
  4. temperatureat reflux temperature
  5. temperatureto cool
  6. washwashed with ethyl acetate
  7. additionThe filtrate was treated with water so that two phases
  8. customwere formed
  9. customThe aqueous phase was separated off
  10. extractionextracted twice with ethyl acetate
  11. washThe combined organic phases were washed with water
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-3a97a70f978f4f5d954e97f583559991
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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