Dimethylformamide → 7-[(2,4-Dichlorophenyl)methyl]pyrrolo[3,2-f]quinazoline-1,3-diamine

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Reaction Steps

A suspension of 7.97 g. of 7-H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 500 ml. of dry dimethylformamide is stirred under nitrogen as 4.61 g. of ca. 50% sodium hydride-mineral oil dispersion is added carefully. After stirring for 1.5 hours, a solution of 8.99 g. of 2,4-dichlorobenzyl chloride in 30 ml. of dry dimethylformamide is added during ca. 10 minutes. Stirring is continued for 5 hours and then 25 ml. of glacial acetic acid is added to the reaction mixture. After removal of solvent (in vacuo), the residue is stirred throughly with a mixture of excess aqueous potassium carbonate solution and 100 ml. of 1 N sodium hydroxide solution and filtered. The crude product is dissolved in 5 liters of boiling methanol, treated with charcoal, and filtered through Celite. The filtrate is concentrated to ca. 500 ml. and chilled. The crystalline solid is collected and again recrystallized from methanol to afford 6.33 g. of the title compound, m.p. 249°-250° C., NMR (dDMSO and D2O): δ 5.58 (singlet, N--CH2 --C6H3Cl2), 6.68 (doublet, J=8 Hz, 5H), 7.10 (doublet, J=3 Hz, 9H), 7.52 (doublet, J=3 Hz, 8H), 7.68 (doublet, J=8 Hz, 6H) p.p.m.; λmax95%EtOH 258 mμ (26,000) and 315 mμ (8,500).

Provenance & Evidence