3-bromo-6-nitroquinoline synthesis
- Product Name:3-bromo-6-nitroquinoline
- CAS Number:7101-95-3
- Molecular formula:C9H5BrN2O2
- Molecular Weight:253
Yield: 38.2%
Reaction Conditions:
with acetic acid at 110; for 2 h;Skraup Quinoline Synthesis;
Steps:
4.1.2.1.53. 3-Bromo-6-nitroquinoline (32)
4-nitroaniline (5.0 g,36.2 mmol) in acetic acid (35 mL) was treated with 2,2,3 tribromopropanal(11.7 g, 39.8 mmol) and the mixture was heated at110 °C for 2 h. AcOH was evaporated in vacuum followed byextraction of crude with ethyl acetate and water. Organic layer waswashed with sat. NaHCO3 and brine, respectively and dried overNa2SO4. Crude product was purified by column chromatographyusing ethyl acetate and hexane as eluting solvents; Yield =38.2%(3.5 g); 1H NMR (400 MHz, DMSO-d6) δ 9.23 (dt, J =17.1, 8.6 Hz, 1H),9.14 (d, J= 2.4 Hz, 1H), 8.89-8.73 (m, 2H), 7.86 (dd, J=8.3, 4.2 Hz,1H); HRMS Calculated for C9H6BrN2O2+ m/z 252.9607, found mass= 252.9611.
References:
Contreras, Jacob I.;Ezell, Edward L.;Garrison, Jered C.;Kizhake, Smitha;Mallareddy, Jayapal Reddy;Napoleon, John V.;Natarajan, Amarnath;Radhakrishnan, Prakash;Rajesh, Christabelle;Rana, Sandeep;Sagar, Satish;Singh, Sarbjit;Sonawane, Yogesh A. [European Journal of Medicinal Chemistry,2021,vol. 222]
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