2-Chloroquinoxaline

White to grey to purple or light brown powder

2-Chloroquinoxaline is used as a reagent to synthesize Chloroquinoxaline sulfamide, a compound that is active against human cancers. 2-Chloroquinoxaline is also used as a starting material to synthesize a variety of novel arylaminoquinoxalines, a group of compounds that exhibit antimalarial activity in rats.

The chlorination of the 2-hydroxy quinoxaline was carried out in neat POCl3 (2.3 eqs) at reflux for an hour and produced the 2-chloro-quinoxaline (1D-008) in very good yield. This chemistry was tested on 100 g scale and afforded typically 103-105 g (98-99percent). A quick filtration through a Pad of silica of the crude reaction mixture resulted in clean material (99percent pure by LCMS). This reaction has beenscaled up to 600 g.The 2.000g2-hydroxy quinoxaline in 20mL phenylphosphonic dichloride, under nitrogen conditions, 110 ° C reflux 12h. The reaction was monitored by TLC. After completion of the reaction, the reaction solution was cooled to room temperature, poured into ice water slowly with constant stirring. product After precipitation, filtration, washing, drying, you can get 1.830g2- chloro quinoxaline (intermediate II-1), a yield of 81percent.Place 2-hydroxyquinoxaline (2 g) and phosphorus oxychloride (20 mL) in 100 mLIn a three-neck flask, add 5 drops of DMF, and transfer the system to reflux for 2h.In a 500 mL beaker, add an appropriate amount of ice water. White solids precipitated, Yield 75percent.2-hydroxyquinoxaline (2 g) and phosphorus oxychloride (20 mL) were placed in 100 mL of threeStir in the bottle, add 5 drops of DMF, reflux for 2 h, transfer the system to a 500 mL beaker, and add an appropriate amount of ice water. Precipitating whiteSolid, yield 75percentGeneral procedure: 0.13 mL of N, N-dimethylformamide was added dropwise to a slurry monohydroxy quinoxaline 1d-e (0.5g, 3.1 mmol) and thionyl chloride (0.73 g, 6.2 mmol) in 1-chlorobutane(5 mL). The resulting reaction mixture was refluxed for 15min., and then evaporated to dryness under reduced pressure to leave a solid. The residue was taken up in a minimum of CH2Cl2, filtered and washed with CH2Cl2. Concentration then give the halogenated derivatives.General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr

Molecular Weight:164.59
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Exact Mass:164.0141259
Monoisotopic Mass:164.0141259
Topological Polar Surface Area:25.8
Heavy Atom Count:11
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes