Sodium borohydride → HCID 68182226, compound

Participants

Reaction Steps

To a stirred solution of N-(2-(3-formyl-6-methoxyquinolin-2-ylamino)ethyl)acetamide SLA 41168 (0.70 g, 2.43 mmol) in THF (30 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.09 g, 2.43 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, the mixture was basified to pH=9 using a 2 N aq. NaOH solution. THF was 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 to give N-(2-(3-(hydroxymethyl)-6-methoxyquinolin-2-ylamino)ethyl)acetamide SLA 41174 as an orange solid (0.65 g, 93% yield).

Provenance & Evidence