2-Chloro-5-nitro-3-(trifluoromethyl)pyridine → 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

HRID 545072Notes

Reaction equation

HRID 545072 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1.[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:12])=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

6

Reactant 2

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridineHCID 5284359Calcium Chloride

Product 1

HCID 135322446-Chloro-5-(trifluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Heat a mixture of 2-chloro-5-nitro-3-trifluoromethyl-pyridine (2.27 g, 10 mmol), calcium chloride (1.1 g, 10 mmol) and iron powder (4.5 g) in ethanol (30 mL) and water (5 mL) at reflux for 1 hour. Cool the mixture and filter through Celite. Evaporate the filtrate, dissolve the residue in EtOAc (200 mL) and wash with saturated NaHCO3(aq) (100 mL) and brine (100 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 1 hour
  3. temperatureCool the mixture
  4. filtrationfilter through Celite
  5. customEvaporate the filtrate
  6. dissolutiondissolve the residue in EtOAc (200 mL)
  7. washwash with saturated NaHCO3(aq) (100 mL) and brine (100 mL)
  8. customDry the
  9. extractionorganic extract over MgSO4
  10. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-c228b34c3a074790ad74b0874218dd10
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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