2,4-DICHLORO-3-NITRO-QUINOLINE

Preparation of compound 2-3 To a solution of 2-2 (10 g, 48.5 mmol) in POC13 (80 mL) was added Et3N (4.85 g, 48.5 mmol). The solution was heated to 120°C and stirred for 3 hrs, and then the solvent was removed in vacuum. The residue was poured into ice-water, and extracted with DCM. The organic phase was washed with NaHCO3 and brine, and dried over anhydrous Na2SO4 and filtered. The filtration was concentrated and the desired productwas obtained (30 g, 68percent).Triethylamine (60 mL, 44 g, 0.44 mol, 3 eq.) was slowly added to 300 mL of POCh at room temperature. The mixture was heated to 90 °C. Nitro-diol II (30 g, 145 mmol, 1 eq.) was slowly added to the mixture in 1 g portions over 30 minutes. The mixture was then heated at 90 °C for 45 minutes. The mixture was then cooled to 0 °C and ice and cooled water was added to the mixture with vigorous stirring until it reached 1.2 L total volume. The mixture was stirred vigorously and then the aqueous mother liquor was decanted and 1 L of water was added to the remaining dark solid. The walls of the flask were scraped to remove the sticky solid and create a suspension, and then filtered. The solid was resuspended in one liter of water and then solid NaHCC was slowly added until the pH was greater than 6. The solid was filtered out and then dissolved in 500 mL of EtOAc. The crude solid was filtered to remove insoluble impurities. The filtrate was washed with saturated NaHCCb, water, and brine, and then separated. The organic layer was dried with Na(2)2, 4-dichloro-3-nitroquinoline(2)2, 4-dichloro-3-nitroquinolineA mixture of 2, 4-dihydroxy-3-nitroquinoline (23 gm, 0.112 moles), and diisopropylethylamine (22.3 gm, 30 mL, 0.172 moles) was stirred in toluene (100 mL) and cooled in an ice bath. To this mixture was added phosphorous oxychloride (67.4 gm, 41 mL, 0.440 moles) through a dropping funnel over 15 minutes. Once the addition was complete, the brown solution was heated at reflux for 10 hours. After cooling, the reaction solution was stirred in ice and water (800 gm) and a solution of potassium carbonate (80 gm) in water (200 mL) was slowly and cautiously (foaming) added. After stirring for 60 minutes, ethyl acetate (200 mL was added and the organic phase was isolated. The aqueous was extracted with ethyl acetate (200 mL) and these extracts were combined with the original organic phase. The combined organic solutions were washed with 20percent potassium carbonate solution before being dried over magnesium sulfate. After filtration, the solvents were removed under vacuum. The residual brown solid was recrystallized from 2-propanol. After filtration and washing with 2-propanol followed by hexane, the brown solid was dried under vacuum. The yield was 15.5 gm (56.9percent).Compound 11v (3 g, 14.5 mmol) was dissolved in 20 mL of phenylphosphonyl dichlorideand heated at 135 C for 3 h. The reaction mixture was pouredinto ice-water and stirred vigorously to obtain the precipitate, which was filtered and dried to afford the compound 12v (1.90 g, 54.0percent).1H NMR (400 MHz, CDCl3) d 8.27 (d, J = 8.1 Hz, 1H), 8.11(d, J = 8.1 Hz, 1H), 7.95 (t, J = 7.2 Hz, 1H), 7.81 (t, J = 7.2 Hz, 1H).ESI-MS: calcd for [M+H]+ m/z 243.0, found: 243.0.A mixture of 2, 4-dihydroxy-3-nitroquinoline (5.08 g, 24.7 mmol) and phenylphosphonic dichloride (13.9 mL, 98.4 mmol) was heated at 140 °C for 3 hr. After the mixture had cooled somewhat, it was added to 18.5 g of NaHC0

Molecular Weight:243.04
XLogP3:3.6
Hydrogen Bond Acceptor Count:3
Exact Mass:241.9649828
Monoisotopic Mass:241.9649828
Topological Polar Surface Area:58.7
Heavy Atom Count:15
Complexity:259
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes