Dimethylformamide → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	7-Bromo-1,2,3,4-tetrahydroquinolin-2-one	HCID 27281844	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Chloroform	HCID 6212	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-Oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile	HCID 58686845	—

Reaction Conditions

Temperature	180 °C

Reaction Steps

To a DMF solution (14.5 mL) of the compound (3.00 g) obtained in Step 1-2, zinc cyanide (1.04 g), Pd2(dba)3 (122 mg), Xantphos (154 mg) and TMEDA (590 μL) were added and the mixture was stirred under microwave irradiation (180° C.) for 5 minutes. To the reaction mixture, CHCl3 was added and the mixture was filtrated by Celite and washed with DMF. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane=50/50 to 100/0; v/v). To the solid substance obtained, EtOAc was added at room temperature and the mixture was stirred for 30 minutes. A solid substance was obtained by filtration and washed with EtOAc to obtain 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile (15.5 g, a light yellow solid).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08461182B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-d4ca4a8f32e04ec0a9afec4685e2576f
Source note	uspto-grants-2013_06