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

HRID 2304566Notes

Reaction equation

HRID 2304566 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

A suspension of 2-chloro-3-quinolinecarbaldehyde (19.2 g, 100 mmol) in methanol (400 ml) is treated with sodium borohydride (5.7 g, 150 mmol). After agitation for 2 hours at ambient temperature, the reaction medium is concentrated under reduced pressure then taken up in water, filtered, washed with water and with ethanol in order to produce, after drying under reduced pressure, 15.8 g (81%) of a white solid, m.p. 166° C.

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. filtrationfiltered
  3. washwashed with water and with ethanol in order
  4. customto produce
  5. dry with materialafter drying under reduced pressure, 15.8 g (81%) of a white solid, m.p. 166° C.

Sources & evidence

ORD record
ord-5f6161128e4045928e69e9f91c8f9598
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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