2-Chloro-3-quinolinecarboxaldehyde → (2-chloroquinolin-3-yl)methanol

HRID 577015Notes

Reaction equation

HRID 577015 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 930708(2-chloroquinolin-3-yl)methanolYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloroquinoline-3-carbaldehyde (1.0 g, 5.21 mmol) in anhydrous ethanol (20 mL) at 0° C., was added sodium borohydride (0.197 g, 5.21 mmol). The reaction mixture was stirred at the same temperature for 1 hour. After completion of the reaction, as monitored by TLC and HPLC, the reaction mixture was quenched with water. The solvent was evaporated, and the crude residue was extracted with dichloromethane. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate to provide the (2-chloroquinolin-3-yl)methanol as a white solid (0.96 g, 95% yield); M+ 193.64.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with water
  3. customThe solvent was evaporated
  4. extractionthe crude residue was extracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-d1cce9d9fd9b4cb1af9e3a685a2eda9b
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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