Toluene → HCID 23292973, compound

HRID 2080061Notes

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([CH3:30])[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>[CH2:30]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH2:23])[CH:9]=1)[C:24]1[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 4-bromobenzonitrile (10 g, 55.3 mmol) and benzylamine (11.8 g, 0.11 mol) in toluene (100 mL) under nitrogen atmosphere, and the solution was stirred at 80° C. for 5 hours. The reaction solution was allowed to room temperature, then, filtrated 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-benzyl amino-benzonitrile (11.1 g, 96%) was obtained as a yellow solid.

Workup

customwas allowed to room temperature
filtrationfiltrated 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-f1213f621e4b4ad09e7832397dc27058
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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