Nitric Acid → (4-Hydroxy-3-methoxy-5-nitrophenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone

HRID 42645Notes

Reaction equation

HRID 42645 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([C:16]([F:19])([F:18])[F:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:4][C:3]=1[O:20][CH3:21].[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[OH:1][C:2]1[C:7]([N+:22]([O-:24])=[O:23])=[CH:6][C:5]([C:8]([C:10]2[C:11]([C:16]([F:17])([F:18])[F:19])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:4][C:3]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 68703345(4-Hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone

Product 1

HCID 68702642(4-Hydroxy-3-methoxy-5-nitrophenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (4-hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone (0.472 g, 1.59 mmol) in acetic acid (10 mL) at room temperature was added 60% nitric acid (0.14 mL, 1.75 mmol) dropwise. The resulting mixture was allowed to stir for thirty minutes then poured onto ice-water (100 mL) and the resulting precipitate was filtered off, washed with water and dried. Recrystallisation from ethanol afforded (4-hydroxy-3-methoxy-5-nitrophenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone as a yellow solid, 0.315 g (58%).

Workup

  1. additionthen poured onto ice-water (100 mL)
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-eaca1b99178a44069ee4bd593bee4087
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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