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

HRID 539469Notes

Reaction equation

HRID 539469 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ClCCl>C1(C)C(C)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[C:21]1([NH:20][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 6344DichloromethaneHCID 111155062-(3-Bromophenyl)pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 68023588N-phenyl-3-(pyridin-2-yl)anilineYield 86%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 7237O-XyleneSolvent

Procedure

2-(3-bromophenyl)pyridine (4 g, 17.09 mmol), Pd2(dba)3 (0.156 g, 0.171 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (0.281 g, 0.683 mmol), and sodium t-butoxide (2.463 g, 25.6 mmol) were mixed in 100 mL of xylene. The solution was bubbled with nitrogen for 20 min. Aniline (2.387 g, 25.6 mmol) was added. The reaction was heated up to reflux for 6 h. After cooled to rt, dichloromethane was added. The mixture was filtered through Celite®. The solvent was then evaporated. The residue was coated on Celite® and columned with 1:5 hexanes/ethyl acetate to give N-phenyl-3-(pyridin-2-yl)aniline (3.6 g, 14.62 mmol, 86% yield) as light yellow solid.

Workup

  1. customThe solution was bubbled with nitrogen for 20 min
  2. temperatureThe reaction was heated up
  3. temperatureto reflux for 6 h
  4. filtrationThe mixture was filtered through Celite®
  5. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-5d01ae38b3514e6fa2bf1e2c1de2bc1f
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

Loading…