Methyl iodide → HCID 15662867, compound

Participants

Reaction Steps

A mixture of 6-benzyloxy-1,2,3,4,5-pentamethoxy-9-acridone (2.257 g, 5 mmol), K2CO3 (3.0 g) and methyl iodide (2.128 g, 15 mmol) in acetone (60 ml) was heated under reflux for 20 hours. After cooling to room temperature, the mixture was filtered and washed with acetone. The combined filtrate and washings are evaporated in vacuo to dryness. The residue was dissolved in chloroform (60 ml), and the solution is washed with water (30 ml×3), dried over sodium sulfate, and concentrated to dryness. The residue was crystallized from ethanol to give 6-benzyloxy-10-methyl-1,2,3,4,5-pentamethoxy-9-acridone, 2.007 g (89%), mp 127-8 ° C. 1H-NMR (CDCl3): δ3.70, 3.87, 3.91, 3.93, 3.98, and 4.10 (each 3H, s, 5×OMe, 1×NMe), 5.24 (2H, s, CH2), 6.96 (1H, d, J=9.05 Hz, H-7), 7.32- 7.48 (5H, m Ph), 8.01 (1H, d, J=9.05, H-8). Analyses: Calculated for C25H27NO7 : C, 66.21; H, 6.00; N, 3.09. Found: C, 65.99; H, 6.18; N, 3.11.

Provenance & Evidence