3-(Trifluoromethyl)aniline → HCID 71678214, compound

HRID 1469747Notes

Reaction equation

HRID 1469747 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]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>O>[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[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 71678214HCID 71678214, compoundYield 156.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-8-nitroquinoline (step-2, Intermediate-11, 100 mg, 0.48 mmol) and 3-(trifluoromethyl)aniline (309 mg, 1.92 mmol) was heated at 150° C. for 20 minutes in microwave. Then water was added to the reaction mixture and it was extracted with CHCl3. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 250 mg of the title product.

Workup

  1. extractionwas extracted with CHCl3
  2. washThe organic layer was washed with brine
  3. customseparated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2d6f86cf10234d1ab37743acb1c83eea
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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