Sodium Methoxide → 5-(Methoxymethyl)quinolin-8-ol

HRID 23937

Reaction equation

HRID 23937 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.[CH3:15][O-:16].[Na+]>CO>[CH3:15][O:16][CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 6901295-(Methoxymethyl)quinolin-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloromethyl-8-hydroxyquinoline hydrochloride (2.145 g; 9.3 mmol) was added to a mixture of sodium methoxide (1.763 g; 32.6 mmol) in MeOH (40 ml). The reaction mixture was stirred for about 4 h at room temperature, and then evaporated to dryness. The residue was dissolved in CHCl3 (100 ml, the solution was washed with water until a neutral pH was obtained, and was then washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was extracted with hexane (100 ml). The hexane solution was evaporated to give the title product, 0.36 g (20%). M.p. 75-760° C. TLC (CHCl3/MeOH/NH3.9.5:0.5:0.1). Rf=0.36.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in CHCl3 (100 ml
  3. washthe solution was washed with water until a neutral pH
  4. customwas obtained
  5. washwas then washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. extractionThe residue was extracted with hexane (100 ml)
  9. customThe hexane solution was evaporated

Sources & evidence

ORD record
ord-2ec5d463dceb4791969bf473db271151
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Linked notes

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