Sodium Hydroxide → 6-Methyl-5-nitroisoquinoline

HRID 1051245Notes

Reaction equation

HRID 1051245 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
0 °C

Procedure

6-Methylisoquinoline (46.3 g, 0.323 mol) obtained in Step (1) was mixed with sulfuric acid (400 mL) and stirred. The temperature of the reaction solution was cooled to 0° C. or lower, slowly added with potassium nitrate (65.3 g, 0.646 mol) and stirred for 3 hours or more at 0° C. The reaction mixture was added with an ice water, and adjusted to have a pH value of 12 by adding 5N aqueous NaOH solution, followed by stirring for 12 hours or more at room temperature. The solid thus obtained was filtered under reduced pressure, and the resulting 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. stirringstirred for 3 hours or more at 0° C
  2. stirringby stirring for 12 hours or more at room temperature
  3. customThe solid thus obtained
  4. filtrationwas filtered under reduced pressure
  5. washthe resulting solid was washed with water
  6. customThe filtered solid was dried
  7. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Sources & evidence

ORD record
ord-c7a40b236a6e41f282693da01be221e7
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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