Acetone → 6-Hydroxymethylquinoline

HRID 1815176Notes

Reaction equation

HRID 1815176 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].CC(C)=O.[O-]S([O-])(=O)=O.[Mg+2]>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 180AcetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 736812Methyl quinoline-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15143856-Hydroxymethylquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Similar to the method described by C. Kaslow and W. Clark, (JOC 18, 55, 1953), to a stirred solution of methyl quinoline-6-carboxylate (10 g, 53 mmol) in THF (200 mL) at 0° C. was added LiAlH4 (1.3 g, 14.9 mmol) by small portion. The resulting mixture was stirred at 0° C. for 2 h then warmed to RT and stirred for 3 h. Acetone (10 mL) was added followed by MgSO4×10H2O. The resulting mixture was stirred for 1.5 h at RT and filtered over a silica pad. Solvents were removed to give the crude quinolin-6-yl-methanol.

Workup

  1. temperaturethen warmed to RT
  2. stirringstirred for 3 h
  3. stirringThe resulting mixture was stirred for 1.5 h at RT
  4. filtrationfiltered over a silica pad
  5. customSolvents were removed

Sources & evidence

ORD record
ord-63db1eda9cb842938634dd598a7b21e7
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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