Ammonium Chloride → 1-[1,8]Naphthyridin-4-yl-ethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

[1,8]Naphthyridine-4-carbaldehyde (0.300 g, 1.90 mmol) was dissolved in a mixture of anhydrous toluene (10 mL) and anhydrous THF (10 mL). The solution was cooled to 0° C. and methyl magnesium bromide (1.62 mL of 1.4M in THF/toluene) was added slowly and the solution stirred 1 h while allowing to warm to RT. Satd. aq. ammonium chloride was added until the solution reached a bright yellow color and precipitate was apparent. The solution was passed through a syringe filter and into water, where it was extracted with EtOAc (3×30 mL). The combined organic fractions were dried over Na2SO4, filtered, and concentrated under vacuum. The product was purified (SGC using MeCN:hexanes eluant in 1:1 ratio initially, then switching to DCM:MeOH:NH4OH eluant in 89:10:1 ratio to finish the compound elution) yielding the title compound (0.079 g). MS (ESI+) for m/z 175 (M+H)+. 1H NMR (CDCl3) δ 8.73 (m, 1H), 8.64 (d, 1H), 8.38 (m, 1H), 7.52 (d, 1H), 7.25 (dd, 1H), 6.32 (bs, 1H), 5.58 (dd, 1H), 1.48 (s, 3H).

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