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

HRID 2246193Notes

Reaction equation

HRID 2246193 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+]>CO>[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)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-3-formylquinoline (6 g; 21.3 mmol) in 150 mL of methanol was added sodium borohydride (1.8 g; 46.97 mmol) and was stirred at room temperature for 16 hours. Methanol was removed by rotary evaporation. The residue was re-suspended in chloroform, washed with water and dried over potassium carbonate. After filtration through a silica gel pad, the product, 2-chloro-3-hydroxymethylquinoline was present as a white solid (4.3 g), which was used for the next synthesis step without further purification.

Workup

  1. customMethanol was removed by rotary evaporation
  2. washwashed with water
  3. dry with materialdried over potassium carbonate
  4. filtrationAfter filtration through a silica gel pad
  5. customwas used for the next synthesis step without further purification

Sources & evidence

ORD record
ord-9012826e8f8948b8a68ac4f910e0b9ec
Source dataset
uspto-grants-2010_03
Patent number
US07687487B2

Reaction notes

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