Water → 6-Hydroxymethylquinoline

HRID 1959619Notes

Reaction equation

HRID 1959619 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](OC)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.CCOCC>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][OH:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 736812Methyl quinoline-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15143856-HydroxymethylquinolineYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl quinoline-6-carboxylate (14 g, 74.8 mmol) in THF (80 mL) was added LiAlH4 (2.84 g, 74.8 mmol) in portions. The reaction was stirred at rt for 20 min. Then water (2.84 mL) and aqueous NaOH (10%, 4.26 mL) were added dropwise to quench the reaction. After stirring for additional 20 min, ether was added and the resulting mixture was filtered through celite. The filtrate was concentrated in vacuo to give a residue which was purified by column chromatography with hexane/EtOAc to afford quinolin-6-ylmethanol (7.6 g, 64%).

Workup

  1. customto quench
  2. customthe reaction
  3. stirringAfter stirring for additional 20 min
  4. filtrationthe resulting mixture was filtered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue which
  7. customwas purified by column chromatography with hexane/EtOAc

Sources & evidence

ORD record
ord-a66af330fc3f4e5783a0a2b5021a2527
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

Loading…