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

HRID 530920Notes

Reaction equation

HRID 530920 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-175a8674dd1e474c9c21c000b5b300ee
Source dataset
uspto-grants-2016_05
Patent number
US09353110B2

Reaction notes

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