Potassium Carbonate → 3-Methyl-5-nitroisoquinoline

HRID 490286

Reaction equation

HRID 490286 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N+:12]([O-])([O-:14])=[O:13].[K+].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143063-MethylisoquinolineHCID 24434Potassium Nitrate

Product 1

HCID 2749733-Methyl-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 3-methylisoquinoline (5.4 g, 0.04 mol) in concentrated sulfuric acid (30 ml) was cautiously added to a solution of potassium nitrate (4.25 g, 1.1 eq) in concentrated sulfuric acid (23 ml) whilst maintaining the temperature below 4° C. (ice bath). Stirring was continued for 2 h and then temperature raised to ambient. Reaction was further stirred for 3 h and then poured into ice-water slurry (500 mL. Neutralisation using solid potassium carbonate affored a yellow solid which was filtered and washed with water. This material was dissolved in ethanol (200 mL, filtered and concentrated under reduced pressure to afford the title compound as a yellow solid.

Workup

  1. temperaturewhilst maintaining the temperature below 4° C. (ice bath)
  2. temperaturetemperature raised to ambient
  3. customReaction
  4. stirringwas further stirred for 3 h
  5. filtrationwas filtered
  6. washwashed with water
  7. dissolutionThis material was dissolved in ethanol (200 mL
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6050edcef1e643b3910406caa6fddefc
Source dataset
uspto-grants-2009_05
Patent number
US07528150B2

Linked notes

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