Pyrazole → 7-nitro-3-(1H-pyrazol-1-yl)quinoline

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	N,N,2-trimethylaziridine-1-carboxamide	HCID 11007919	—
Reactant	3-Iodo-7-nitroquinoline	HCID 68618821	—
Catalyst	Copper iodide	HCID 83717	—
Solvent	Water	HCID 962	—
Product	7-nitro-3-(1H-pyrazol-1-yl)quinoline	HCID 68618824	99.9%

Reaction Conditions

Temperature	70 °C

Reaction Steps

Pyrazole (20 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (24 μl), copper iodide (14 mg), and cesium carbonate (73 mg) were added to an N,N-dimethylpropyleneurea (2 ml) solution containing 3-iodo-7-nitroquinoline (45 mg), followed by stirring at 70° C. for 2.5 hours in a nitrogen atmosphere. Water was added to the reaction solution, an insoluble precipitate was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 0:1), and a light yellow solid of 7-nitro-3-(1H-pyrazol-1-yl)quinoline (36 mg) was thus obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08895585B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-54b5fa05b94f4dc6b41458968b5a1eb6
Source note	uspto-grants-2014_11