Calcium Chloride → 6'-Chloro-3-(trifluoromethyl)[2,3'-bipyridin]-5'-amine

HRID 1791244Notes

Reaction equation

HRID 1791244 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:18]([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH2:18]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 22030137HCID 22030137, compound

Product 1

HCID 220300306'-Chloro-3-(trifluoromethyl)[2,3'-bipyridin]-5'-amineYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6′-chloro-5′-nitro-3-trifluoromethyl-[2,3′]bipyridinyl (25 g, 0.082 mol) and calcium chloride (11 g, 0.1 mol) in ethanol (300 mL) and water (50 mL), add iron powder (45 g, 0.82 mol). Heat the solution to reflux for 1.5 hours, cool and filter through Celite. Concentrate the mixture under reduced pressure, re-dissolve in ethyl acetate (300 mL) and wash with brine (200 mL). Concentrate the solution under reduced pressure and purify by flash chromatography on silica gel (50% ether/50% hexane) to give the title compound (19 g, 85%) as a pale yellow solid.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 1.5 hours
  3. temperaturecool
  4. filtrationfilter through Celite
  5. concentrationConcentrate the mixture under reduced pressure
  6. dissolutionre-dissolve in ethyl acetate (300 mL)
  7. washwash with brine (200 mL)
  8. concentrationConcentrate the solution under reduced pressure
  9. custompurify by flash chromatography on silica gel (50% ether/50% hexane)

Sources & evidence

ORD record
ord-b1a11252fbf44ab2a075573749a25439
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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