Potassium Carbonate → HCID 54230499, compound

Participants

Reaction Steps

3-Hydroxyacridine-9-carboxylic acid methyl ester (14.6 g; 57.7 mmol) was dissolved in 500 ml DMF, then potassium carbonate (25.0 g; 181 mmol) and m-nitrobenzylbromide (15.0 g; 69.4 mmol) were added and stirred at room temperature. After 4 hours the mixture was filtered and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in CH2Cl2 and washed with HCl 1N, NaOH 1N and sodium chloride solution (10%). After drying with sodium sulfate and evaporating to dryness the residue was flash chromatographed (column: 10 cm diameter) in CH2Cl2 +1% methanol (fractions of 200 ml). Fractions 7-23 were combined, evaporated and the residue was collected on a Buchner funnel and washed with diethylether. Yield 8.7 g (39%), Fp.>250° C. 1H-NMR(CDCl3): 5,35(2H, s, CH2) and 4,22 ppm (3H, s, CH3). MS: M+ =388.

Provenance & Evidence