Sodium borohydride → (6-Ethoxy-2-(ethylamino)quinolin-3-yl)methanol
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH2:15][CH3:16])[C:8]([CH:17]=[O:18])=[CH:7]2)[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH2:15][CH3:16])[C:8]([CH2:17][OH:18])=[CH:7]2)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 6-ethoxy-2-(ethylamino)quinoline-3-carbaldehyde SLA 41034 (0.605 g, 2.48 mmol) in THF (50 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.094 g, 2.48 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-ethoxy-2-(ethylamino)quinolin-3-yl)methanol SLA 41040 as an orange solid (481 mg, 79% 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-e1171a1f4ca44c57a5433b8fff729372
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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