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

HRID 1724847Notes

Reaction equation

HRID 1724847 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-2125d00ef3bc483485d30afcb2ea4b38
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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