Sodium borohydride → (6-Methoxy-2-(2-methoxyethylamino)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][O:16][CH3:17])[C:7]([CH:18]=[O:19])=[CH:6]2.[BH4-].[Na+]>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][O:16][CH3:17])[C:7]([CH2:18][OH:19])=[CH:6]2Participants
Procedure
To a stirred solution of 6-methoxy-2-(2-methoxyethylamino)quinoline-3-carbaldehyde SLA 47060 (0.895 g, 3.4 mmol) in THF (34 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.13 g, 3.4 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 (10 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-(2-methoxyethylamino)quinolin-3-yl)methanol SLA 47064A as a yellow oil (0.90 g, 100% yield).
Workup
- temperaturethen cooled in an ice bath
- custombefore quenching by addition of a 1 N aq. HCl solution (10 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-60b22054597d4adcb31c772b075b71fa
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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