Potassium Hydroxide → 3,3''-Dimethyl-1',2',3',4',5',6'-hexahydro-[2,2'; 6',2'']terpyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3″-dimethyl-2′,3′,5′,6′-tetrahydro-1′H-[2,2′;6′,2″]terpyridin-4′-one (9.6 g, 34.1 mmol) in diethylene glycol (170 mL) was added hydrazine monohydrate (90 mL, 2.89 mol) and potassium hydroxide pellets (57.4 g, 1.02 mol) and the reaction stirred at 125° C. for 2 hours. 50 mL of hydrazine distilled off and water (200 mL) was added the remaining mixture. The solution was extracted with CH2Cl2 (4×300 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in EtOAc (500 mL) and washed with a saturated solution of NaHCO3 (3×100 mL) to remove the residual diethylene glycol. The organic extract was dried (MgSO4) and concentrated under reduced pressure to afford 8.82 g (97%) of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine as yellow solid. 1H NMR (CDCl3) δ 1.50-1.65 (m, 2H), 1.75-1.95 (m, 3H), 2.13 (m, 1H), 2.37 (s, 6H), 3.09 (br t, 1H), 4.15-4.25 (m, 2H), 7.02 (dd, 2H, J=7.5, 4.8 Hz) 7.38 (d, 2H, J=7.5 Hz), 8.46 (br d, 2H).

Provenance & Evidence