3-(Trifluoromethyl)phenol → 8-Nitro-4-(3-(trifluoromethyl)phenoxy)quinoline

HRID 1469734Notes

Reaction equation

HRID 1469734 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[N+:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 866922328-Nitro-4-(3-(trifluoromethyl)phenoxy)quinolineYield 37.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-chloro-8-nitroquinoline (200 mg, 0.96 mmol), 3-(trifluoromethyl)phenol (250 mg, 1.54 mmol), K2CO3 (414 mg, 2.99 mmol) in CH3CN (2 mL) was heated in a sealed tube at 100° C. for 8 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 120 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.83 (d, J=5.4 Hz, 1H), 8.60-8.57 (d, J=8.4 Hz, 1H), 8.36 (d, J=6.9 Hz, 1H), 7.85-7.73 (m, 5H), 6.87 (d, J=5.4 Hz, 1H).

Workup

  1. customThen the reaction mixture was quenched with water
  2. extractionwas extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6af45d456dd64c779d5bff0e51af0524
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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