3-Quinolinecarboxaldehyde → (Quinolin-3-yl)methanol

HRID 1684407Notes

Reaction equation

HRID 1684407 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[CH:2]=1.[BH4-].[Na+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:12])[CH:2]=1

Participants

4

Reactant 2

HCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanolYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.14 g (20 mmol) of 3-quinolinecarboxaldehyde in 60 mL of methanol was added portion-wise 0.95 g (25 mmol) of sodium borohydride at 0° C. The reaction mixture was then stirred at room temperature for 2 hours. Excess sodium borohydride was quenched with acetic acid and the reaction mixture was evaporated in vacuo. The residue was dissolved in dilute aqueous sodium bicarbonate and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated in vacuo to give an oil. The oil was chromatographed on silica gel, using first 3:2 chloroform/ethyl acetate and then ethyl acetate as eluents, to afford 2.35 g (79.5%) of the title compound of the structural formula ##STR65## The product was characterized as follows: TLC Rf =0.30 (ethyl acetate); IR (neat) ν 3120, 1580, 1500, 1060 cm-1 ; NMR (CDCl3) δ 8.73 (1H d, J=2 Hz) 8.07 (1H, s), 8.02 (1H, d, J=7 Hz), 7.8-7.3 (3H, m), 4.82 (2H, s).

Workup

  1. customExcess sodium borohydride was quenched with acetic acid
  2. customthe reaction mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dilute aqueous sodium bicarbonate
  4. extractionextracted three times with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give an oil
  9. customThe oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-417172c81f8644d197c08f0c676c2ab8
Source dataset
uspto-grants-1997_06
Patent number
US05639885

Reaction notes

Loading…