Water → (Quinolin-3-yl)methanol

HRID 1915162Notes

Reaction equation

HRID 1915162 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+].O>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

5

Reactant 3

HCID 962WaterHCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Quinolinecarbaldehyde (2.00 g, 12.7 mmol) was dissolved in 25 mL of methanol. To this solution was added sodium borohydride (0.24 g, 6.4 mmol) in small portions over a period of 20 minutes. Then 2 mL of water were added and the mixture was evaporated. The residue was dissolved in ethyl acetate (75 mL) and washed with water (3×75 mL), dried (MgSO4) and evaporated, providing 1.8 g of quinolin-3-yl-methanol in 90% yield; 1H NMR (DMSO-d6) δ 4.89 (s, 2H), 7.53 (t, J=7.1 Hz, 1H), 7.64-7.71 (m, 1H), 7.77 (d, J=8.2 Hz, 1H), 8.04-8.12 (m, 2H), 8.83 (d, J=2.0 Hz, 1H).

Workup

  1. customthe mixture was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (75 mL)
  3. washwashed with water (3×75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-05c14f878eee479ea06e2535b39f5a82
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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