Potassium Nitrate → 4-Methyl-5-nitroisoquinoline

HRID 1858910Notes

Reaction equation

HRID 1858910 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O.O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-:14])=[O:13])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 24434Potassium NitrateHCID 640939Isoquinoline, 4-methyl-

Product 1

HCID 221219294-Methyl-5-nitroisoquinolineYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

To 45 ml of concentrated sulfuric acid was added 12.75 g of 4-methylisoquinoline (produced according to Tetrahedron, 1982, 38, 3347) under ice-cooling, and a solution of 9.02 g of potassium nitrate in 34 ml of concentrated sulfuric acid was added dropwise at a temperature not exceeding 0° C. After 30 minutes of stirring, the reaction mixture was poured in iced water containing aqueous ammonia and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to provide 12.0 g of light-yellow crystals.

Workup

  1. temperaturecooling
  2. customexceeding 0° C
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a25438ea35094b3ca89a3326fab44195
Source dataset
uspto-grants-2000_11
Patent number
US06153608

Reaction notes

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