2-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde → (2-(Ethylamino)-6-methoxyquinolin-3-yl)methanol

Participants

Reaction Steps

To a stirred solution of SLA 28162 (1.495 g, 6.49 mmol) in THF (120 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.246 g, 6.50 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 (40 mL). After stirring for 15 min at RT, 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 at 40° C. under vacuum to give (2-(ethylamino)-6-methoxyquinolin-3-yl)methanol SLA 28164 as an orange oil (1.17 g, 78% yield).

Provenance & Evidence