Iodine → HCID 21465560, compound

Participants

Reaction Conditions

Reaction Steps

To an eggplant type flask (500 ml), 3-dimethylamino-4',6'-dimethoxy-2'-hydroxyacrylophenone (5.026 g) prepared in Example 15 and methyl alcohol (200 ml) were added. The mixture was dissolvedby heating at 80° C. for 10 minutes with stirring. After the solution was cooled, iodine (10.152 g) was slowly added. After 15 minutes, the disappearance of the starting material was confirmed by thin layer chromatography. To the reaction mixture, methylene chloride (700 ml) and then 5% aqueous solution of sodium thiosulfate (200 ml) were added to reduce iodine. The organic layer was separated, and washed with distilled water (100 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1 to 1/2), and recrystallized from ether to give the titled compound (3.43 g; yield=34.5%) as colorless crystals. Melting point: 158°-160° C. 1H-NMR(CDCl3, δ ppm): 3.88 (s, 3H, OMe), 3.93 (s, 3H, OMe), 6.38 (s, 1H, ArH), 6.42 (s, 1H, ArH), 8.06 (s, 1H, H2).

Provenance & Evidence