Acetone → 2-Chloro-6-methoxyquinoline-3-methanol

HRID 2390895Notes

Reaction equation

HRID 2390895 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.CO.[BH4-].[Na+].CC(C)=O>C(OCC)(=O)C.O>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 8651102-Chloro-6-methoxyquinoline-3-methanolYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of 2-chloro-6-methoxy-3-quinolinecarbaldehyde (3.1 g, 14 mmol) and methanol (10 ml), sodium borohydride (530 mg, 14 mmol) was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 30 minutes. Acetone was added to the reaction mixture at the same temperature, followed by the addition of water and ethyl acetate at the same temperature. The organic layer was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=1:1), thereby obtaining the entitled compound (3.0 g, 98%).

Workup

  1. additionwas added at 0° C. (an outer temperature), and
  2. customthe obtained reaction mixture
  3. customThe organic layer was separated
  4. washwashed with saturated saline
  5. customThe solvents were evaporated under reduced pressure from the organic layer
  6. customthe obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1cc24feea67542aebeb9cf594365e573
Source dataset
uspto-grants-2012_09
Patent number
US08273885B2

Reaction notes

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