3-BROMO-8-NITROQUINOLINE synthesis
- Product Name:3-BROMO-8-NITROQUINOLINE
- CAS Number:5341-07-1
- Molecular formula:C9H5BrN2O2
- Molecular Weight:253.05
Yield: 42% ， 0.054 g
Reaction Conditions:
with N-Bromosuccinimide;acetic acid at 100; for 2 h;
Steps:
2 Example 2. Synthesis of 3-Bromo-8-nitroguinoline.
To 5 mL of acetic acid were added 8-nitroquinoline (0.2 g, 1.15 mmol) and Nbromosuccinimide (0.102 g, 0.575 mmol). The solution was heated to reflux for 2 h, cooled to ambient temperature, and poured over 20 mL of water. The crude product was collected by filtration, washed with cold water and air dried. The crude product (a mixture ofmonobrominated, dibrominated, and unbrominated material) was purified by column chromatography (9 g) using 3:1 hexane/ethyl acetate as the eluent. Chromatography gave 2 as a white solid (0.121 g, 42% yield, mp 122 °C, lit mp 123 °C) as well as the 3,6-dibromo-8- nitroquinoline (0.054 g, mp: 179 °C). 1H NMR (400MHz, CDCI3) O 9.05 (1H, 5), 8.43 (1H, 5), 8.05-8.07(1H, d, J= 7.2 Hz), 7.97(1H, d, J= 8.8 Hz), 7.7(1H, t, J= 8.0 Hz) for 2. 1H NMR(400MHz, CDCI3) O 9.04 (1H, d, J= 1.2 Hz), 8.34 (1H, d, J= 2.4 Hz), 8.12 (2H, d, J= 1.2 Hz) for 3,6-dibromo-8-nitroquinoline.
References:
NORTHEASTERN UNIVERSITY;HANSON, Robert, N. WO2016/183578, 2016, A1 Location in patent:Page/Page column 11; 12
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