3-Bromo-8-quinolinamine

To a solution of compound 121 (22.00 g, 86.94 mmol) obtained by process 1 in ethanol (1100- ml) were added water (66 ml), concentrated hydrochloric acid (66 ml) and iron powder (24.28 g, 434.8 mmol) at room temperature. The reaction mixture was refluxed for 1 hour and cooled to room temperature, and the insoluble materials were filtered off by passing through Celite pad. To the residue obtained by evaporation under reduced pressure were added 10 percent sodium hydrogen carbonate solution (700 ml) and ethyl acetate (500 ml), and the mixture was stirred for 30 minutes. The insoluble materials . were filtered off by passing through Celite pad, and the organic layer obtained by filtration was washed with brine, dried over magnesium sulfate and decolorized with activated carbon. The solvent was concentrated under reduced pressure to give compound 122 (18.11 g, 81.19 mmol, 93.4percent) as pale yellow crystals.Intermediate 2 (0.847 g, 3.3 mmol) was dissolved in 30 mL of acetic acid-water (2:1), followed by the addition of iron powder (0.935 g, 16.7 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. Solvent was removed by rotary evaporation; theproduct mixture was suspended in dichloromethane and filtered through CELITE to remove iron salts. The resultant solid was purified by column chromatography on silica gel (35 g) using dichloromethane as the eluent. Fractions containing the product were combined, evaporated to dryness to yield 4 as a yellow solid 0.45 g (60 percent yield, mp 104 °C, lit mp = 106-107 °C). 1H NMR (400MHz, CDCI3) O 8.72 (1H, d, J= 2.4 Hz), 8.21 (1H, d, J= 2.0 Hz), 7.32-7.38 (1H, t, J= 8.0 Hz), 7.06 (1H, d, J= 8.0 Hz), 6.92 (1H, d, J= 7.2 Hz), 4.8-5.2 (3H, 5).

Molecular Weight:223.07
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:221.97926
Monoisotopic Mass:221.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes