2-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde → (2-(Ethylamino)-6-methoxyquinolin-3-yl)methanol

HRID 1620205Notes

Reaction equation

HRID 1620205 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2]>C1COCC1>[CH2:1]([NH:3][C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 866698182-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 68182241(2-(Ethylamino)-6-methoxyquinolin-3-yl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of SLA 28162 (1.495 g, 6.49 mmol) in THF (120 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (0.246 g, 6.50 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 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 at 40° C. under vacuum to give (2-(ethylamino)-6-methoxyquinolin-3-yl)methanol SLA 28164 as an orange oil (1.17 g, 78% 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 at 40° C. under vacuum

Sources & evidence

ORD record
ord-cfe2a5db29ef46c9b73beadc74acd1f3
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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