Sodium borohydride → HCID 68182168, compound

Participants

Reaction Steps

To a solution of 6-ethoxy-2-(ethylamino)-7-fluoroquinoline-3-carbaldehyde SMA 44102 (63 mg, 0.24 mmol) in THF (10 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (11 mg, 0.29 mmol) and the reaction mixture was stirred for 3 h at RT, then cooled down to 0° C. and quenched with a 6 N aq. HCl solution (5 mL). The mixture was stirred for 10 min at RT before basification to pH=12 with a 10 N aq. NaOH. THF was then removed at 40° C. and the residue was extracted with CH2Cl2 (30 mL). The organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum to give (6-ethoxy-2-(ethylamino)-7-fluoroquinolin-3-yl)methanol SMA 44104 as a pink solid (61 mg, 96% yield).

Provenance & Evidence