Hydrochloric Acid → (2-(Dimethylamino)-6-methylquinolin-3-yl)methanol

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Reaction Steps

To a stirred solution of 2-(dimethylamino)-6-methylquinoline-3-carbaldehyde RBO 35148 (988 mg, 4.61 mmol) in a mixture EtOH:THF=50 mL:20 mL in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (174 mg, 4.61 mmol) and the mixture was stirred overnight at RT, cooled in an ice bath and treated by a 6 N aq. HCl solution (2 mL). After stirring for 1 h at 4° C., the mixture was brought to pH=9 with a 2N aq. NaOH solution (6 mL). Volatiles were removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (50 mL). The organic layer was washed with water (3×20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give (2-(dimethylamino)-6-methylquinolin-3-yl)methanol RBO 40152 as yellow oil (900 mg, 90% yield).

Provenance & Evidence