8-CHLORO-3-IODOQUINOLINE

N-LODOSUCCINIMIDE (67.9 g, 0.30 MMOL) was added in portions to a stirred solution of 8- chloroquinoline (49 g, 0.30 MMOL) (J. Org. CHEM., 1987, 52, 1673-80) in acetic acid (300 ml) at 70 °C under argon. The mixture was heated to 70 °C for 18 h and then CONCENTRATED IN VACUO. The residue was redissolved in DICHLOROMETHANE (600 ml) and the solution was washed successively with 10percent aqueous sodium thiosulfate solution (2 x 300 ML) and 10percent aqueous sodium hydrogen carbonate solution (2 x 300 ML), dried (MGS04) and CONCENTRATED IN VACUO to a solid. The solid was recrystallised from ethyl acetate to afford the title compound (D1) as a yellow solid (42 g, 0.145 mol, 48percent). The residue from recrystallisation was purified by chromatography over silica gel eluting with a toluene/acetone gradient to afford a second crop of the product (18 g, total yield 69percent). SH (CDC13) 7.49 (1H, t, J = 8. 1HZ), 7.65 (1H, dd, J = 1.4Hz, 8.3Hz), 7.85 (1H, dd, J = 1.3Hz, 7.4Hz), 8.57 (1H, d, J = 2. 1 Hz), 9.15 (1 H, D J = 2. 1 HZ). Mass Spectrum: C9H5CIIN requires 289, 291 ; found 290, 292 (MH+)Description 1 8-CHLORO-3-IODOQUINOLINE (D1) N-lodosuccinimide (67.9 g, 0.30 MMOL) was added in portions to a stirred solution of 8- CHLOROQUINOLINE (49 g, 0.30 MMOL) (J. Org. Chem. , 1987, 52, 1673-80) in acetic acid (300 ml) at 70 °C under argon. The mixture was heated to 70 °C for 18 h and then concentrated in vacuo. The residue was REDISSOLVED in dichloromethane (600 ml) and the solution was washed successively with 10percent aqueous sodium thiosulfate solution (2 x 300 ml) and 10percent aqueous sodium hydrogen carbonate solution (2 x 300 ML), dried (MGS04) and concentrated in vacuo to a solid. The solid was recrystallised from ethyl acetate to afford the title compound (D1) as a yellow solid (42 g, 0.145 mol, 48percent). The residue from recrystallisation was purified by chromatography over silica gel eluting with a TOLUENE/ACETONE gradient to afford a second crop of the product (18 g, total yield 69percent).Description 10; 8-Chloro-3-iodoquinoline (D10); N-lodosuccinimide (206.3g, 0.92mol) was added portionwise over 1 h to a stirred solution of 8-chloroquinoline (15Og, 0.92mol) in acetic acid (750ml) at 4ODescription 3; 8-Chloro-3-iodoquinoline (D3); N-lodosuccinimide (206.3 g, 0.92 mol) was added portionwise over 1 h to a stirred solution of 8-chloroquinoline (150 g, 0.92 mol) in acetic acid (750 ml) at 40°C. The reaction temperature was then increased to 65°C and this was maintained for 18 h after which another portion of N-iodosuccinimide (61.9 g, 0.28 mmol) was added. After a further 4 h at this temperature, the mixture was cooled to ambient temperature and evaporated in vacuo to an oil. The oil was dissolved in dichloromethane (600 ml) and the solution was washed with saturated sodium thiosulfate solution (2 x 400 ml), dried (MgS04) and concentrated in vacuo to a solid (280 g). The solid was recrystallized from ethyl acetate (300 ml) to afford the title compound (D3) as a yellow solid (80 g). Concentration of the corresponding filtrate gave a second crop of title compound (30 g, total yield 45percent). MS: m/z (M+H)@ C9H5CIIN requires 289, 291; found 290, 292 (MH+).N-Iodosuccinimide (206 3g, 0 92mol) was added portionwise over Ih to a stirred solution of 8-chloroquinoline (15Og, 0 92mol) in acetic acid (750ml) at 40

Molecular Weight:289.50
XLogP3:3.1
Hydrogen Bond Acceptor Count:1
Exact Mass:288.91552
Monoisotopic Mass:288.91552
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes