Aniline → N-phenyl-3-(quinolin-2-yl)aniline

HRID 539475Notes

Reaction equation

HRID 539475 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[CH:10]=[C:11]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH:12]=[CH:13][CH:14]=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:2]1([NH:1][C:13]2[CH:14]=[CH:9][CH:10]=[C:11]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 156059482-(3-Chlorophenyl)quinolineHCID 23676156Sodium t-butoxide

Product 1

HCID 70654371N-phenyl-3-(quinolin-2-yl)anilineYield 46.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Aniline (2.75 g, 29.6 mmol), 2-(3-chlorophenyl)quinoline (5.25 g, 21.90 mmol), sodium tert-butoxide (3.36 g, 35.0 mmol), Pd2dba3 (0.501 g, 0.548 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybephenyl (S-Phos) (0.898 g, 2.190 mmol) were charged into the reaction flask with 200 mL of toluene. This mixture was evacuated and back-filled with nitrogen then was heated at reflux for 20 h. The reaction mixture was cooled to room temperature then was diluted with 200 mL of water. The toluene layer was separated and the aqueous was extracted with 100 mL of toluene. The organic extracts were combined and removed under vacuum. The crude residue was passed through a silica gel column using 75% DCM/hexanes then was passed through a silica gel column using 1-5% ethyl acetate/DCM. The clean product fractions were combined and solvents were removed under vacuum yielding N-phenyl-3-(quinolin-2-yl)aniline (3 g, 10.12 mmol, 46.2% yield).

Workup

  1. customThis mixture was evacuated
  2. additionback-filled with nitrogen
  3. temperaturethen was heated
  4. temperatureat reflux for 20 h
  5. additionthen was diluted with 200 mL of water
  6. customThe toluene layer was separated
  7. extractionthe aqueous was extracted with 100 mL of toluene
  8. customremoved under vacuum
  9. customsolvents were removed under vacuum

Sources & evidence

ORD record
ord-05307e51ba364c18b088796e4bc09239
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

Loading…