Acetic Acid → N2-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridine-2,3-diamine

HRID 2273330Notes

Reaction equation

HRID 2273330 reaction equation
O.C(O)(=O)C.[N+:6]([C:9]1[C:10]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)([O-])=O>[Fe].C(O)C>[F:24][C:21]([F:22])([F:23])[CH2:20][NH:19][C:10]1[C:9]([NH2:6])=[CH:14][C:13]([C:15]([F:16])([F:17])[F:18])=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 86725178(3-Nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl)amine

Product 1

HCID 86725179N2-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridine-2,3-diamineYield 96.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of an iron powder (2.12 g), ethanol 6 ml), water 4 ml) and acetic acid 0.1 ml) was added dropwise a mixture of (3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl)amine (1.83 g) and ethanol (10 ml) at 70° C., and then the mixture was stirred at 70° C. for 1 hour. After allowing to cool, the cooled reaction mixture was filtrated. To the filtrate was added water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give N2-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine (1.59 g).

Workup

  1. additionwas added dropwise
  2. temperatureto cool
  3. customthe cooled reaction mixture
  4. filtrationwas filtrated
  5. additionTo the filtrate was added water
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-582b34d142b7486b89c1d6db94aa4ec0
Source dataset
uspto-grants-2015_09
Patent number
US09120823B2

Reaction notes

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