4-AMINO-2-BROMOQUINOLINE

4-AMINO-2-BROMOQUINOLINE Property

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Appearance

White to light yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

4-AMINO-2-BROMOQUINOLINE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-bromoquinolin-4-amines from 2-bromo-3-nitroquinolines is as follows: compound 5 was prepared by reference to literature methods [Kornblum, N. et al. Reduction of optically active 2-nitrooctane and α-phenylnitroethane. J. Am. Chem. Soc. 1955, 77, 6266-6269; Den Hertog, H. J.; Buurman, D. J. Rec. Trav. Chim. Pays-Bas 1972, 91, 841-849]. The procedure was as follows: compound 4 (1.82 g, 7.2 mmol) was dissolved in acetic acid, iron powder (5 eq.) was added, and the reaction mixture was stirred at 65 °C for 2.5 hours. After completion of the reaction, the iron powder was removed by filtration and washed with dichloromethane (DCM). Subsequently, the pH was adjusted to 9 with 2 M sodium hydroxide solution, filtered again and the residue was washed with ammonia. The aqueous layer was extracted with dichloromethane and the organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The product was purified by column chromatography using dichloromethane as eluent. The target product was obtained as 0.69 g in 43% yield. The structure of the product was confirmed by 1H NMR (CDCl3) and 13C NMR (CDCl3): 1H NMR (CDCl3) δ 4.81 (broad peak, 2H, NH2), 6.76 (single peak, 1H, Ar), 7.48 (triple peak, 1H, J = 7.3 Hz, Ar), 7.62-7.73 (multiple peaks, 2H, Ar), 7.94 (double peaks) , 1H, J = 8.76 Hz, Ar); 13C NMR (CDCl3) δ 106.65, 117.82, 120.21, 125.37, 129.19, 130.45, 148.78, 150.90.

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 926 - 931
[2] Patent: WO2010/20981, 2010, A1. Location in patent: Page/Page column 29; 1/2