Ammonium Chloride → 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine

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Reaction Steps

To a suspension of the diester (1) (3.0 g, 10.0 mmol) in 200 mL of absolute ethanol, 8.2 g of sodium borohydride was added in one portion. The mixture was refluxed for 3 hours, cooled to room temperature, then 200 mL of a saturated aqueous solution of ammonium chloride was added to decompose the excess borohydride. The ethanol was removed and the precipitated solid was dissolved with a minimum amount of water. The resulting solution was extracted with ethyl acetate (5×200 mL) then dried over sodium sulfate and rotary-evaporated. The 1.7 g (80% yield) of solid (2) thus obtained was used without further purification. 1H NMR (300 MHz, CD3OD) δ ppm: 4.75 (4H, s, 2CH2OH), 7.43 (2H, d, 3JHH=6 Hz, aryl H on C5 and C5′), 8.25 (2H, s, aryl H on C3 and C3′), 9.00 (2H, d, 3JHH=6 Hz, aryl H on C6 and C6′). Elemental analysis of C12H12N2O2: calcd. C 66.65, H 5.59, N 12.95%, found C 65.90, H 5.70, N 12.32%.

Provenance & Evidence