Acetone → 6-Hydroxymethylquinoline

HRID 2251835Notes

Reaction equation

HRID 2251835 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(C)=O.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[N:11]1[C:12]2[C:7](=[CH:6][C:5]([CH2:3][OH:2])=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=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

Following the procedure described by C. Kaslow and W. Clark, JOC 18:55 (1953), to a stirred solution of quinoline-6-carboxylic acid methyl ester (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 and at RT 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 quinolin-6-yl-methanol.

Workup

  1. stirringThe resulting mixture was stirred for 1.5 h at RT
  2. filtrationfiltered over a silica pad
  3. customSolvents were removed

Sources & evidence

ORD record
ord-2f9ddb3c238740b59e82dc4efa9f0059
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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