Water → 2-Quinolinemethanol

HRID 709570Notes

Reaction equation

HRID 709570 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[BH4-].[Na+].O>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 796192-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 731962-QuinolinemethanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-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) and evaporated. The residue was chromatographed in CH2Cl2-methanol gradient, eluting the product at 97:3 CH2Cl2-methanol, and providing 1.7 g of quinolin-2-yl-methanol in 85% yield; 1H NMR (CDCl3) δ 4.92 (s, 2H), 7.26 (d, J=2.1 Hz, 1H), 7.30-7.57 (m, 1H), 7.68-7.75 (m, 1H), 7.82 (dd, J=8.0 Hz, J=0.9 Hz, 1H), 8.07 (d, J=8.4 Hz, 1H), 8.13 (d, J=8.5 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. customevaporated
  5. customThe residue was chromatographed in CH2Cl2-methanol gradient
  6. washeluting the product at 97:3 CH2Cl2-methanol

Sources & evidence

ORD record
ord-08e88d41a42d458b9a4f6e748cd15586
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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