Methanol → 4-Methoxyquinoline

HRID 39728

Reaction equation

HRID 39728 reaction equation
CO.[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[CH:14](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C.CCCCCC>C(#N)C>[CH3:14][O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 86587183Trimethylsilyldiazomethane hexaneHCID 178516385quinolin-4-ol

Product 1

HCID 5219384-Methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 15 mL of methanol containing 4.02 g of 4-hydroxyquinoline and 130 mL of an acetonitrile solution, 5.01 g of diisopropylethylamine and 19.4 mL of a 2.0 mol/L trimethylsilyldiazomethane/hexane solution were added at room temperature, and the mixture was stirred for 13 hours, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate 2:1] to obtain 1.79 g of a yellow oily substance, 4-methoxyquinoline.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate 2:1]

Sources & evidence

ORD record
ord-02d91b4db9784466a5b7377a1c928c93
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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