Nitric Acid → HCID 22030083, compound

HRID 1791264Notes

Reaction equation

HRID 1791264 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:4]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[N+:18]([C:13]1[C:12](=[O:15])[NH:11][CH:10]=[C:9]([C:4]2[C:3]([C:2]([F:16])([F:1])[F:17])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22030009HCID 22030009, compound

Product 1

HCID 22030083HCID 22030083, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 3-trifluoromethyl-1′H-[2,3′]bipyridinyl-6′-one (25 g, 0.1 mol) in concentrated sulfuric acid (100 mL) at 0° C., add dropwise a solution of fuming nitric acid (35 mL) and concentrated sulfuric acid (10 mL). Heat the reaction mixture to 70° C. for 1 hour, cool and pour onto ice (500 mL). Filter the mixture and treat the filtrate with 10 M sodium hydroxide until the solution is at pH 4-5. Collect the precipitate by filtration and air dry to give the title compound (26.2 g, 92%) as a white solid.

Workup

  1. temperaturecool
  2. additionpour onto ice (500 mL)
  3. filtrationFilter the mixture
  4. additiontreat the filtrate with 10 M sodium hydroxide until the solution
  5. customCollect the precipitate
  6. filtrationby filtration and air
  7. customdry

Sources & evidence

ORD record
ord-05492f6a96b7429db4e0da67867767ff
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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