Trifluoroacetic acid → 3-(3,4-Dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)isoxazole

HRID 61997Notes

Reaction equation

HRID 61997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]2[CH:18]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:17](O)[O:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]2[C:18]([C:19]3[C:20]([C:25]([F:27])([F:28])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:17][O:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68703434HCID 68703434, compound

Product 1

HCID 687050003-(3,4-Dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)isoxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(3,4-dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)-4,5-dihydroisoxazol-5-ol (2.06 g, 5 mmol) was heated in 20 mL of ethyl acetate to 70° C. To the resulting slurry was added trifluoroacetic acid (0.74 g, 6.5 mmol) dropwise. After 10 minutes, the reaction was evaporated to dryness and the residue was recrystallised from isopropanol to give 3-(3,4-dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)isoxazole, 1.224 g (62%).

Workup

  1. customthe reaction was evaporated to dryness
  2. customthe residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-bd979ee7e95e46799defbc1727b138ad
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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