ChemicalBook CAS DataBase List 6-NITROQUINOLINE

6-NITROQUINOLINE synthesis

9synthesis methods

Product Name:6-NITROQUINOLINE
CAS Number:613-50-3
Molecular formula:C9H6N2O2
Molecular Weight:174.16

612-57-7 Synthesis

612-57-7
221 suppliers
$6.00/1g

613-50-3
242 suppliers
$10.00/5g

Yield:613-50-3 97%

Reaction Conditions:

with Tris(3,6-dioxaheptyl)amine;sodium nitrite;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;t-BuBrettPhos in tert-butyl alcohol at 130; for 24 h;Product distribution / selectivity;Inert atmosphere;

Steps:

54
EXAMPLE FIFTY-FOUR: General Procdure for Pd-Catalyzed Nitrations of Aryl Chlorides and Aryl Sulfonates (Figures 20 and 21); An oven-dried schlenk tube, which was equipped with a magnetic stir bar and fitted with a rubber septum, was charged with the Pd₂(dba)₃ (0.5 mol %), ligand (6, 25, 26, or 27) (1.2 mol %), and NaNO₂ (138 mg, 2.0 mmol) (aryl halides* that were solids at room temperature were added with the catalyst). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then the aryl halide* (1.0 mmol), tris(3,6-dioxaheptyl)amine (5 mol %), and te/t-butanol (2 mL) were added via syringe. The reaction vessel was sealed with a Teflon screw cap and heated to 110 ⁰C for 24 h. The solution was cooled to room temperature, diluted with Ethyl acetate, washed with water, and purified via flash chromatography.* Includes aryltriflates and arylnonaflates.

References:

MASSACHUSETTS INSTITUTE OF TECHNOLOGY WO2009/76622, 2009, A2 Location in patent:Page/Page column 144-145

FullText