4-Tert-Butylaniline → (4-tert-Butyl-phenyl)-[7-(2-trifluoromethyl-phenyl)-quinolin-4-yl]-amine

HRID 968561Notes

Reaction equation

HRID 968561 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]([F:21])([F:20])[F:19])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:22]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>CC(O)C>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([NH:30][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:18]([F:21])([F:20])[F:19])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:31][CH:32]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 22030439HCID 22030439, compound

Product 1

HCID 22030258(4-tert-Butyl-phenyl)-[7-(2-trifluoromethyl-phenyl)-quinolin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Heat a mixture of 4-chloro-7-(2-trifluoromethyl-phenyl)-quinoline (42 mg, 0.14 mmol) and 4-(tert-butyl)aniline (41 mg, 0.29 mmol) in 2-propanol (10 mL) at reflux for 3 hours. Evaporate the mixture, add 1M NaOH (10 mL), extract twice with EtOAc (10 mL each), dry (Na2SO4), and evaporate to provide the crude product. Purify by silica gel chromatography, eluting with 75% hexane-EtOAc to provide (4-tert-Butyl-phenyl)-[7-(2-trifluoromethyl-phenyl)-quinolin-4-yl]-amine as a white solid. Mass spec. 420.2.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 hours
  3. customEvaporate the mixture
  4. additionadd 1M NaOH (10 mL)
  5. extractionextract twice with EtOAc (10 mL each)
  6. dry with materialdry (Na2SO4)
  7. customevaporate
  8. customto provide the crude product
  9. customPurify by silica gel chromatography
  10. washeluting with 75% hexane-EtOAc

Sources & evidence

ORD record
ord-6c007b966d7648bab5a51c645ac98a69
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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