Water → 6-Hydroxymethylquinoline

HRID 456047

Reaction equation

HRID 456047 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>[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

6

Reactant 4

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

Product 1

HCID 15143856-HydroxymethylquinolineYield 64%

Reagents, catalysts & solvents 1

HCID 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. Then water (2.84 mL) and NaOH (10%, 4.26 mL) was added dropwise to quench excess reducing agent. After stirring for additional 20 min, ether was added, and the resulting mixture was filtered through celite. The filtrate was concentrated to a residue, which was purified by silica gel with hexanes:EtOAc to afford quinolin-6-ylmethanol (7.6 g) in 64% yield.

Workup

  1. customto quench excess
  2. additionether was added
  3. filtrationthe resulting mixture was filtered through celite
  4. concentrationThe filtrate was concentrated to a residue, which
  5. customwas purified by silica gel with hexanes

Sources & evidence

ORD record
ord-1745be2e8a53480babfcf54e00f43f1a
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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