Methanol → HCID 15218810, compound

Participants

Reaction Conditions

Reaction Steps

6,6"-Dicyano-4'-(4-methoxyphenyl)-2,2':6',2"-terpyridine (1.556 g, 4.0 mmole) prepared in example 14 was dissolved in Ultrex acetic acid (130 mL, Baker) in a Parr hydrogenation bottle by warming to 50° C. for 25 minutes. The solution was sparged with argon for 5 minutes, 10% Pd/C (470 mg) was added under argon, and the reaction mixture was hydrogenated at 45 psi and 45° C. for 19 hours in a Parr hydrogenation apparatus. After venting excess hydrogen and replacing it with argon, the catalyst was removed by filtration using 5 mL of acetic acid as a wash. Most of the solvent was then evaporated under reduced pressure at 35° C. Residual acetic acid was removed by a series of consecutive additions and co-evaporations using 2×30 mL aliquots of toluene, then 2×30 mL aliquots of methylene chloride, and finally 2×30 mL aliquots of ethanol. The product was then dried under vacuum at 30° C. overnight to give 2.3 g (99.5 % recovery) of product as an off-white solid. Thin layer chromatography (silica gel; 85% methylene chloride, 5% methanol, 10% NH4OH, v/v/v) showed the desired product as a spot with an Rf of 0.3 (with some streaking) plus a trace amount of a small spot at the origin. Infrared and mass spectra were in good agreement for the desired product. 1H NMR (DMSO-D6) 3.85 (s, 3H, OCH3), 4.07 (s, 4H, CH2 --N), 7.16 (d, 2H), 7.55 (d, 2H), 7.99 (d, 2H), 8.03 (t, 2H), 8.52 (d, 2H) and 8.78 ppm (s, 2H).

Provenance & Evidence