Potassium Nitrate → 4-Methoxy-3-nitroisoquinoline

HRID 878766Notes

Reaction equation

HRID 878766 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5][CH:4]=1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 37854894-Methoxyisoquinoline

Product 1

HCID 682896234-Methoxy-3-nitroisoquinolineYield 35%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-methoxyisoquinoline (130 mg, 0.82 mmol) in 98% sulfuric acid (0.61 mL) was added potassium nitrate (91 mg, 0.90 mmol), and the mixture was heated to 60° C. and stirred for 2 hours. The reaction solution was cooled, and then thereto was added ice. The powders were filtered to dissolve in ethyl acetate. The solution was washed with aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate, followed by concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:8) to give 4-methoxy-3-nitroisoquinoline (58.3 mg, 35%) as a pale yellow powder.

Workup

  1. temperatureThe reaction solution was cooled
  2. additionwas added ice
  3. filtrationThe powders were filtered
  4. dissolutionto dissolve in ethyl acetate
  5. washThe solution was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationby concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:8)

Sources & evidence

ORD record
ord-87f87aae3b534e50828a6ef432da3898
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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