Sodium Methoxide → 1-Methoxy-7-nitroisoquinoline

HRID 1070465Notes

Reaction equation

HRID 1070465 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:15][O-:16].[Na+]>CO>[CH3:15][O:16][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 218626571-chloro-7-nitroisoquinoline

Product 1

HCID 223970461-Methoxy-7-nitroisoquinolineYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-chloro-7-nitroisoquinoline (670 mg, 3.21 mmol) obtained in Preparation Example 1-5, Step 4 in methanol (100 ml) was added a 1M solution (6.5 ml, 6.5 mmol) of sodium methoxide. The mixture was refluxed under heating for 3 hr and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetone=30:1) to give 1-methoxy-7-nitroisoquinoline (530 mg, 81%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hr
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:acetone=30:1)

Sources & evidence

ORD record
ord-eff2d86e147f4a2caef03d3bd8a359b3
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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