Toluene → 4-PHENYLAMINO-BENZONITRILE

HRID 2080062Notes

Reaction equation

CC(C)([O-])C.[Na+].Br[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C([NH2:23])C1C=CC=CC=1.[C:24]1(C)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1>[C:24]1([NH:23][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of sodium tert-butoxide (7.44 g, 77.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.38 g, 0.415 mmol) and rac-2,2-bis(diphenylphosphino)-1,1-binaphthyl (0.172 g, 0.277 mmol) was added a solution of 4bromobenzonitrile (10 g, 55.3 mmol) and benzylamine (6.5 mL, 0.11 mol) in toluene (100 mL) under nitrogen atmosphere, and the solution was stirred at 80° C. for 5 hours. The reaction mixture was allowed to room temperature, then, filtered through Celite pad to remove insoluble matter, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 4-phenylamino-benzonitrile (6.7 g, 63%) was obtained as a yellow solid.

Workup

customwas allowed to room temperature
filtrationfiltered through Celite pad
customto remove insoluble matter
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-09937303a78b49929e568d10bd71afe2
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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