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

HRID 1791206Notes

Reaction equation

HRID 1791206 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-7d5f6a01c648471eabeceb164af85f3f
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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