Sodium borohydride → (6-Methoxy-2-(2-methoxyethylamino)quinolin-3-yl)methanol

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Reaction Steps

To a stirred solution of 6-methoxy-2-(2-methoxyethylamino)quinoline-3-carbaldehyde SLA 47060 (0.895 g, 3.4 mmol) in THF (34 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.13 g, 3.4 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (10 mL). After stirring for 15 min at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give (6-methoxy-2-(2-methoxyethylamino)quinolin-3-yl)methanol SLA 47064A as a yellow oil (0.90 g, 100% yield).

Provenance & Evidence