6-Methoxy-2-(propylamino)quinoline-3-carbaldehyde → (6-Methoxy-2-(propylamino)quinolin-3-yl)methanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][CH2:14][CH2:15][CH3:16])[C:7]([CH:17]=[O:18])=[CH:6]2>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][CH2:14][CH2:15][CH3:16])[C:7]([CH2:17][OH:18])=[CH:6]2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 6-methoxy-2-(propylamino)quinoline-3-carbaldehyde SLA 28172 (1.565 g, 6.41 mmol) in THF (120 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.242 g, 6.41 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 at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then 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 (6-methoxy-2-(propylamino)quinolin-3-yl)methanol SLA 28174 as an orange solid (1.55 g, 98% yield).
Workup
- temperaturethen cooled in an ice bath
- custombefore quenching by addition of a 1 N aq. HCl solution (40 mL)
- stirringAfter stirring for 15 min at that temperature
- customTHF was then removed at 40° C. under vacuum
- extractionthe solution was extracted with CH2Cl2 (200 mL)
- washwashed with brine (20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-e4b6c9ac8b75454480b1c5912cdd48b3
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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