Biphenyl → 4-Hydroxyquinoline-6-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Biphenyl	HCID 7095	—
Reactant	Diphenyl Ether	HCID 7583	—
Reactant	4-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile	HCID 11694705	—
Solvent	Hexane	HCID 8058	—
Product	4-Hydroxyquinoline-6-carbonitrile	HCID 11658351	90.7%

Reaction Conditions

Temperature	250 °C

Reaction Steps

A mixture of biphenyl (10 ml) and diphenyl ether (30 ml) was heated at 250° C. and 5-(4-cyanophenylamino)methylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (3.28 g) was added thereto. The mixture was stirred for 1 hr. The reaction mixture was cooled to 80° C. while stirring and hexane (100 ml) was added. The mixture was stirred in an ice bath for 0.5 hr. The resulting solid was collected by filtration and washed with hexane to give the object compound (1.86 g) as a yellow-brown powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06348474B1
Source dataset	uspto-grants-2002_02
ORD ID	ord-eb4e478025e747f0bf065ddb1a5809e9
Source note	uspto-grants-2002_02