5,6-Dimethoxy-2-(4-pyridyl)methylene-1-indanone → 5,6-Dimethoxy-2-(pyridin-4-ylmethyl)indan-1-one

Participants

Reaction Conditions

Reaction Steps

1.80 g of 2,3-dihydro-5,6-dimethoxy-2-((pyridin-4-yl)methylene)inden-1-one and 40 milligrams of PtO2 were added to 15 mL glacial acetic acid. The reaction mixture was stirred at 80° C., with H2 being supplied at 1 atmosphere for 6 hours. Solids were filtered off. The filtrate was concentrated. 30 mL of Na2CO3 aqueous solution were added thereto. The resulted mixture was extracted with of chloroform (5×20 mL). The extracts were combined, washed with brine, and dried over anhydrous MgSO4. The drying agent was then filtered off. Solvent was removed in vacuo to give crude product. Purification of crude product by silica gel column chromatography (CHCl3/CH3OH 95/5) afforded 0.63 g of white crystalline compound. The yield was 35%. 1H NMR (CDCl3): 8.53 (brs, 2H), 7.15-7.25 (m, 3H), 6.82 (s, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 3.35 (dd, 1H, J=4.4, 14.0 Hz), 3.12 (dd, 1H, J=7.6, 16.8 Hz), 2.95-3.05 (m, 1H), 2.65-2.75 (m, 2H).

Provenance & Evidence