Diphenylamine → 4-(diphenylamino)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Diphenylamine	HCID 11487	—
Reactant	Benzonitrile, 4-bromo-	HCID 12162	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	4-(diphenylamino)benzonitrile	HCID 9860239	97.3%

Reaction Steps

The above general procedure was followed using 4-bromobenzonitrile (188 mg, 1.03 mmol) and diphenylamine (169 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After one hour, the reaction mixture was adsorbed onto silica gel and chromatographed with 50% toluene/hexanes to give 263 mg (97%) of N-(4-cyanophenyl)diphenylamine as a white solid. 1H NMR (500 MHz, C6D6) δ 6.97 (t, J=8 Hz, 4H), 6.92 (d, J=8.9 Hz, 2H), 6.86-6.83 (m, 6H), 6.56 (d, J=8.7 Hz, 2H). 13C NMR (125 MHz, C6D6) δ 151.3, 146.6, 133.2, 129.9, 126.1, 124.9, 120.5, 119.4, 104.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06100398
Source dataset	uspto-grants-2000_08
ORD ID	ord-abb3262a6ab54d13a96e7e0db22c477a
Source note	uspto-grants-2000_08