Pyridinium chloride → HCID 59770021, compound

Participants

Reaction Conditions

Reaction Steps

Stir a molten mixture of 5-(3-methoxy-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (1.11 g, 3.55 mmol) and pyridine hydrochloride (10 g, 87 mmol) at 215° C. for 40 min. Cool the reaction mixture to 100° C., dilute with 1N HCl, and extract with ethyl acetate. Dry organics (MgSO4), filter, and concentrate to a brown oil containing the title compound. Purification via silica gel chromatography (1:6 ethyl acetate:hexanes) affords 940 mg (89%) of a tan oil. 1H NMR (CDCl3) δ 2.76-3.63 (br m, 4H), 4.59 (s, 1H), 6.45 (s, 1H), 6.64 (m, 2H), 6.75 (s, 1H), 6.99-7.52 (m, 9H); MS (ES) 299 (M+H), 297 (M−H). HPLC shows 97% purity.

Provenance & Evidence