Nitric Acid → HCID 24903131, compound

HRID 923797Notes

Reaction equation

HRID 923797 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=1)[CH3:2].S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20].C(=O)([O-])O.[Na+]>>[CH2:1]([NH:3][C:4]1[C:9]([N+:19]([O-:21])=[O:20])=[CH:8][C:7]([C:10]([F:13])([F:11])[F:12])=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 516892Sodium BicarbonateHCID 13144278N-Ethyl-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 24903131HCID 24903131, compound

Conditions

Temperature
95 °C

Procedure

A mixture of N-ethyl-(5-trifluoromethylpyridin-2-yl)-amine (1.0 g) and sulfuric acid (7 ml) was stirred with heating at 95° C., and then a mixture of fuming nitric acid (0.45 ml) and sulfuric acid (3 ml) were added thereto, and stirred with heating for 1 hour. The reaction mixture cooling to room temperature was poured into ice, and then saturated aqueous sodium hydrogen carbonate solution was poured, 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 chromatography to give 600 mg of N-ethyl-(3-nitro-5-trifluoromethylpyridin-2-yl)-amine.

Workup

  1. additionwere added
  2. stirringstirred
  3. temperaturewith heating for 1 hour
  4. temperatureThe reaction mixture cooling to room temperature
  5. additionwas poured into ice
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68144fa67476488089e36c2288d4a457
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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