HCID 44138603, compound → HCID 68182225, compound

Participants

Reaction Steps

To a stirred solution of 2-(benzylamino)-6-methoxyquinoline-3-carbaldehyde SLA 41002 (0.40 g, 1.37 mmol) in THF (50 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.24 g, 6.35 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 (15 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 (2-(benzylamino)-6-methoxyquinolin-3-yl)methanol SLA 41006 as a yellow solid (0.395 g, 98% yield).

Provenance & Evidence