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4-Bromomethylacridine 6: Acridine 1 (1 g, 5.58 mmol) was dissolved in H2SO4 (20 mL) at 20 °C under N2 and BMME 5 (1.05 g, 7,71 mmol) was added in one portion. The mixture was maintained at 20 °C
for 17 h then it was poured into ice and stirred for 1 h. The precipitated was filtered
off and dissolved in CHCl3. The organic layer was then dried with MgSO4, the solvent was removed under vacuo and the resulting yellow solid was chromatographed
(silica gel, CHCl3/cyclohexane, 7/3, v:v) to give 6 as a bright yellow powder (466 mg, 31%). Mp 166 °C, lit.
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4,5-Bis(bromomethyl)acridine 7: Acridine 1 (2 g, 11.16 mmol) was heated in H2SO4 (25 mL) to 50 °C under N2 and BMME 5 (6.08 g, 44.64 mmol) was added in one portion. The mixture was maintained at 50 °C
for 12 h then it was poured into ice and stirred for 1 h. The precipitated was filtered
off and dissolved in CHCl3. The organic layer was then dried with MgSO4, the solvent was removed under vacuo and the resulting yellow solid was recrystallized
from dry Et2O to give 7 as a bright yellow powder (2.49 g, 64%). Mp 156 °C. 1H NMR (300 MHz, CDCl3): δ = 5.19 (s, 4 H), 7.95 (dd, 1 H, J = 8 Hz), 8.37 (d, 1 H, J = 8 Hz), 8.50 (d, 1 H, J = 8 Hz), 9.91 (s, 1 H). 13C NMR (75 MHz, CDCl3): δ = 27.01, 126.94, 127.59, 128.81, 131.55, 137.83, 139.45, 151.22. Anal. Calcd
for C15H11Br2N: C, 49.35; H, 3.04; N, 3.84. Found: C, 49.49; H, 3,03; N, 3.83.
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<A NAME="RG23603ST-10">10</A>
(5-{[(4-Chlorobenzoyl)oxy]methyl}-4-acridinyl)methyl 4-Chlorobenzoate 9b: A solution of 4-chlorobenzoyl chloride (471 mg, 2.75 mmol) in CH2Cl2 (10 mL) was added dropwise under N2 to a stirred solution of 7 (300 mg, 1.25 mmol), Et3N (0.44 mL, 3.17 mmol) and DMAP (383 mg, 3.14 mmol) in CH2Cl2 (20 mL) at 0 °C. After complete addition, the mixture was allowed to stand at r.t.
for 6 h. The organic layer was then washed with NaOH 1 N (2 × 35 mL), dried with MgSO4 and the solvent was removed under vacuo. The resulting solid was purified by column
chromatography (silica gel, CH2Cl2/EtOAc, 99:1, v:v) to give 9b as a yellow powder (515 mg, 81%). Mp 170 °C. 1H NMR (300 MHz, CDCl3, 25 °C): δ = 6,21 (s, 4 H), 7.35 (m, 4 H), 7.53 (dd, J = 8.5, 6.9 Hz, 2 H), 7.84 (dd, J = 6.9, 0.8 Hz, 2 H), 7.97 (dd, J = 8.5, 0.8 Hz, 2 H), 8.02 (m, 4 H), 8.77 (s, 1 H). 13C NMR (75 MHz, CDCl3, 25 °C): δ = 63.67, 125.50, 126.33, 128.26, 128.67, 128.73, 128.85, 131.10, 134.46,
136.18, 139.31, 146.13, 165.61. Anal. Calcd for C29H19Cl2NO4: C, 67.58; H, 3.71; N, 2.71. Found: C, 67.45; H, 3.70; N, 2.70.
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