Nitric Acid → 2-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)pyridine

HRID 2113607Notes

Reaction equation

HRID 2113607 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[N+:18]([O-])([OH:20])=[O:19]>OS(O)(=O)=O>[CH3:17][C:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:12]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:5][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 220303732-p-Tolyl-3-trifluoromethyl-pyridine

Product 1

HCID 220301282-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-p-tolyl-3-trifluoromethyl-pyridine (8.4 mmol) in H2SO4 (6 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture for 60 minutes at room temperature. Pour the mixture onto ice-water (30 mL), extract with EtOAc, neutralize with 1 N NaOH, dry over Na2SO4, and concentrate under vacuum to obtain 2-(4-methyl-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine.

Workup

  1. additionPour the mixture onto ice-water (30 mL)
  2. extractionextract with EtOAc
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-980dd339d84e47d186aecf6a91c97fca
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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