2,5-Dichloroquinoxaline

Uses

2,5-Dichloroquinoxaline is used in the synthetic preparation of chloroquinoxalines from (chloro)nitroanilines in synthesis of (chloroquinoxalinyloxy)phenoxypropionic acid analogs as antitumor agents.

Definition

ChEBI: 2,5-Dichloroquinoxaline is a quinoxaline derivative.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 1758, 2001 DOI: 10.1021/jm0005149

Synthesis

55687-19-9

55687-05-3

Step 3: 5-chloro-2-hydroxyquinoxaline (0.60 g, 3.32 mmol) was mixed with phosphorus trichloride (10 mL, 109 mmol), heated to 90 °C and maintained for 3 hours. Upon completion of the reaction, the mixture was slowly poured into ice water and subsequently extracted with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a dark brown solid crude product. The crude product was purified by silica gel column chromatography using 0-30% ethyl acetate/hexane gradient elution to give 2,5-dichloroquinoxaline as a white solid (210 mg, 32% yield).

References

[1] Patent: US2010/120778, 2010, A1. Location in patent: Page/Page column 29
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 6,7
[3] Journal of Medicinal Chemistry, 1981, vol. 24, # 1, p. 93 - 101
[4] Patent: DE2433397, 1974,

Raw materials

Preparation Products