Sodium borohydride → (2-(Isopropylamino)-6-methoxyquinolin-3-yl)methanol
Reaction equation
[CH:1]([NH:4][C:5]1[C:14]([CH:15]=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1>[CH:1]([NH:4][C:5]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-(isopropylamino)-6-methoxyquinoline-3-carbaldehyde SLA 28186 (1.55 g, 6.35 mmol) in THF (100 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.24 g, 6.35 mmol) and the mixture was stirred for 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 removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give (2-(isopropylamino)-6-methoxyquinolin-3-yl)methanol SLA 28188 as an orange solid (1.45 g, 93% 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 removed at 40° C. under vacuum
- extractionthe solution was extracted with CH2Cl2 (200 mL)
- washThe organic layer was washed with brine (20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-a8f0cab22aeb4c869cd609cc65170cd1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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