Acetic Acid → HCID 68804532, compound

HRID 923798Notes

Reaction equation

HRID 923798 reaction equation
C(O)(=O)C.O.[CH2:6]([NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][N:10]=1)[CH3:7]>[Fe].C(O)C>[CH2:6]([NH:8][C:9]1[C:14]([NH2:15])=[CH:13][C:12]([C:18]([F:21])([F:19])[F:20])=[CH:11][N:10]=1)[CH3:7]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 24903131HCID 24903131, compound

Product 1

HCID 68804532HCID 68804532, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of iron powder (700 mg), acetic acid (60 μl), ethanol (5 ml), and water (3 ml) was stirred with heating at 70° C., and then a mixture of N-ethyl-(3-nitro-5-trifluoromethylpyridin-2-yl)-amine (490 mg) and ethanol (10 ml) was added dropwise. The mixture was stirred with heating at 70° C. for 3 hours. The reaction mixture cooled to room temperature was filtered through Celite®, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.29 g of N2-ethyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-8).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred
  3. temperaturewith heating at 70° C. for 3 hours
  4. temperatureThe reaction mixture cooled to room temperature
  5. filtrationwas filtered through Celite®
  6. concentrationthe resulting filtrate was concentrated under reduced pressure
  7. additionThe resulting residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30b99808b10d48acabc68df246ea524a
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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