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

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).

1. temperaturecooled in an ice bath
2. stirringAfter stirring for 1 h at 4° C.
3. customVolatiles were removed at 40° C. under vacuum
4. extractionthe solution was extracted with CH2Cl2 (50 mL)
5. washThe organic layer was washed with water (3×20 mL), brine (20 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under vacuum

ORD record

ord-8d6c6ee6cbf540dbb6e983158af7b88f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2