Sodium Hydroxide → 6-Methyl-5-nitroisoquinoline

HRID 1750864Notes

Reaction equation

HRID 1750864 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 6409596-Methylisoquinoline

Product 1

HCID 250590506-Methyl-5-nitroisoquinolineYield 71.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

Sulfuric acid (400 mL) was added to 6-methylisoquinoline (46.3 g, 0.323 mol) obtained in <Step 1> above and the mixture was stirred. The reaction solution was cooled to 0° C. or below, followed by slowly adding potassium nitrate (65.3 g, 0.646 mol). The reaction solution was stirred for 3 hours or more at 0° C. An ice water was poured to the reaction mixture, adjusted to pH 12 by adding 5 N NaOH solution, followed by stirring for 12 hours or more at room temperature. The generated solid was filtered under reduced pressure, and the filtered solid was washed with water. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (43.3 g, 71%).

Workup

  1. customobtained in <Step 1> above and the mixture
  2. temperatureThe reaction solution was cooled to 0° C. or below
  3. stirringThe reaction solution was stirred for 3 hours or more at 0° C
  4. stirringby stirring for 12 hours or more at room temperature
  5. filtrationThe generated solid was filtered under reduced pressure
  6. washthe filtered solid was washed with water
  7. customThe filtered solid was dried

Sources & evidence

ORD record
ord-ee142ce02f704d84a82671a82f836670
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

Loading…