6-Methoxy-2-(methylamino)quinoline-3-carbaldehyde → (6-Methoxy-2-(methylamino)quinolin-3-yl)methanol

HRID 1620197Notes

Reaction equation

HRID 1620197 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][CH3:14])[C:7]([CH:15]=[O:16])=[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][CH3:14])[C:7]([CH2:15][OH:16])=[CH:6]2

Participants

3

Reactant 1

HCID 866698166-Methoxy-2-(methylamino)quinoline-3-carbaldehyde2×

Product 1

HCID 68182278(6-Methoxy-2-(methylamino)quinolin-3-yl)methanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-methoxy-2-(methylamino) quinoline-3-carbaldehyde SLA 28150 (1.006 g, 4.65 mmol) in THF (80 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.176 g, 4.65 mmol) and the mixture was stirred for 4 h 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 RT, 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-(methylamino)quinolin-3-yl)methanol SLA 28152 as an orange oil (0.907 g, 89% yield).

Workup

  1. temperaturethen cooled in an ice bath
  2. custombefore quenching by addition of a 1 N aq. HCl solution (40 mL)
  3. stirringAfter stirring for 15 min at RT
  4. customTHF was then 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

Sources & evidence

ORD record
ord-12067ed4eae540cabec5ec9563dc3e7c
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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