Aniline → 4-PHENYLAMINO-BENZONITRILE

HRID 522426Notes

Reaction equation

HRID 522426 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 6115AnilineHCID 12162Benzonitrile, 4-bromo-HCID 23676156Sodium t-butoxide

Product 1

HCID 99643424-PHENYLAMINO-BENZONITRILE

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a flow of argon, in a 300 mL-recovery flask, 20 g of 4-bromobenzonitrile, 30 mL of aniline, 1.50 g of tris(dibenzylideneacetone)dipalladium(0)[Pd2(dba)3], 2.1 g of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl[BINAP], 21.1 g of sodium tert-butoxide and 313 mL of dehydrated toluene were placed, and reacted at 85° C. for 6 hours.

Workup

  1. customreacted at 85° C. for 6 hours

Sources & evidence

ORD record
ord-0ae08bf92c33462f83269f61884b29b8
Source dataset
uspto-grants-2016_05
Patent number
US09331285B2

Reaction notes

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