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	US06911469B2
Source dataset	uspto-grants-2005_06
ORD ID	ord-6160073082b7493292cbb71fe5dd7b77
Source note	uspto-grants-2005_06