3-Quinolinecarboxaldehyde → (Quinolin-3-yl)methanol

To a stirred solution of quinoline-3-carbaldehyde (1.00 g, 6.36 mmol) in THF (60 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.24 g, 6.36 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. After stirring for 15 min at RT, the mixture was basified to pH=9 with 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 under vacuum to give quinolin-3-ylmethanol SLA 47074A as a yellow oil (1.06 g, >100%). This oil (1.056 g, 6.6 mmol) was dissolved in dry CH2Cl2 (40 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer before dropwise addition of SOCl2 (9.62 mL, 133.3 mmol). The mixture was stirred for 2 h at RT and concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)quinoline hydrochloride SLA 47074B as a yellow solid (1.20 g, 85% yield).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 1 N aq. HCl solution
3. stirringAfter stirring for 15 min at RT
4. customTHF was removed at 40° C. under vacuum
5. extractionthe solution was extracted with CH2Cl2 (200 mL)
6. washwashed with brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum

ORD record

ord-ca5b110a28564bdf8c35807cba89ca75

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2