Water → (8-Methoxyquinolin-5-yl)methanol

HRID 2374166Notes

Reaction equation

HRID 2374166 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](O)=[N:8]2.[C:14](=O)([O-])[O-:15].[K+].[K+].CI.O>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:15][CH3:14])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178519443HCID 178519443, compound

Product 1

HCID 7172171(8-Methoxyquinolin-5-yl)methanolYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Hydroxymethyl) quinolinol (6.7 g, 38 mmol) was dissolved in DMF (38 mL) and treated with potassium carbonate (16 g, 116 mmol) followed by methyl iodide (2.9 mL, 6.8 g, 48 mmol). The mixture was allowed to stir overnight at RT, then poured into a separatory funnel with water and extracted 3× DCM. The organic layer was dried over Na2SO4, and concentrated to give solid 5-hydroxymethyl-8-methoxyquinoline (6.5 g). 1H NMR (CDCl3) δ 8.97 (d, 1H), 8.51 (d, 1H) 7.49 (m, 2H), 6.99 (d, 1H), 5.05 (s, 2H), 4.09 (s, 3H).

Workup

  1. extractionextracted 3× DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2172f9bda830476993ec08712e0f5d53
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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