4-CHLORO-8-NITROQUINOLINE

a. 4-Chloro-8-nitroquinoline (6a). This intermediate was prepared from 4-chloroquinoline (obtained by treating 4-hydroxyquinoline with [POC13] as [4-Chloroquinoline (5 g, 31 mmol) was dissolved in sulfuric acid (23 mL, 0.42 mol), to which nitric acid (4.5 mL, 0.11 mol) was slowly added dropwise, which was then stirred at room temperature for four hours. When the reaction was completed, the resultant was cooled to 0° C., and neutralized with 1M ammonium hydroxide. The generated solid was dissolved in ethyl acetate, dried with anhydrous sodium sulfate, and then filtered. The solvent was removed by vacuum distillation, and the residue was purified by a column chromatography (ethyl acetate/n-hexane=) to obtain 3.55 g of the desired compound as a white solid (yield 55.7percent).To a solution of 4-chloroquinoline (1.0 g, 6.13 mmol) in conc. Ha. 4-Chloro-8-nitroquinoline (6a) and 4-chloro-5-nitroquinoline (6d). 4-Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below [15 °C.] Then the solution was cooled and maintained at-5 °C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 h. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g (59percent) [OF 6A] as golden-brown needles; mp [128-129 °C] (lit. 32 mp [129-130 °C) ; IH NMR (CDC13)] [6] 7.67 (d, 1H, [J=4.] 5), 7.75 (dd, 1H, [J=8.] 6, . [J=7.] 6), 8.10 (dd, 1H, [J=7.] 6, [J=1.] 3), 8. 48 (dd, 1H, [J=8.] 6, J=1. 3), 8.94 (d, 1H, J=4. 5); [13C] NMR (CDC13) [6] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1. The mother liquor was evaporated and chromatographed in 19: 1 hexanes-ethyl acetate, to provide 2.05 g (16percent) of the 5-nitro isomer 6d as a very light yellow solid; mp [144-146 °C] (lit. 31 mp [150 °C) ; IH] NMR (CDCl3) [6] 7.65 (d, 1H, J=4. 7), 7. 82 [(M, ] 2H), 8.35 (dd, [1H, ] [J=2.] 5, J=7. 3), 8.90 (d, 1H, J=4. 7); [13C] NMR [(CDC13)] 8 118.2, 123.4, 125.1, 128.8, 134.2, 135.6, 139.1, 149.7, 151.2.

Molecular Weight:208.60
XLogP3:2.6
Hydrogen Bond Acceptor Count:3
Exact Mass:208.0039551
Monoisotopic Mass:208.0039551
Topological Polar Surface Area:58.7
Heavy Atom Count:14
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes