6-Methoxy-2-(methylamino)quinoline-3-carbaldehyde → (6-Methoxy-2-(methylamino)quinolin-3-yl)methanol

Participants

Reaction Steps

To a stirred solution of 6-methoxy-2-(methylamino) quinoline-3-carbaldehyde SLA 28150 (1.006 g, 4.65 mmol) in THF (80 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.176 g, 4.65 mmol) and the mixture was stirred for 4 h 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 vacuum to give (6-methoxy-2-(methylamino)quinolin-3-yl)methanol SLA 28152 as an orange oil (0.907 g, 89% yield).

Provenance & Evidence