Potassium Iodide → 1-Methyl-5-nitroquinolin-1-ium iodide

HRID 2117319Notes

Reaction equation

HRID 2117319 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].S(OC)(O[CH3:18])(=O)=O.[I-:21].[K+]>O>[I-:21].[CH3:18][N+:9]1[C:10]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6497Dimethyl SulfateHCID 118295-Nitroquinoline

Product 1

HCID 124950501-Methyl-5-nitroquinolin-1-ium iodide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Nitroquinoline (4 g, 30 mmol) was melted at 85° C., prior to addition of dimethyl sulfate (2.2 ml, 30 mmol), and the resulting mixture was stirred at this temperature for 1.5 hours. The yellow gel was dissolved in water (35 ml) and cooled to room temperature. A saturated aqueous solution of potassium iodide (7.63 g, 45.9 mmol) was added, and the resulting orange precipitate was filtered, washing the residue with chilled water. After drying under vacuum at 60° C., for 2 hours, the brick-red solid was used in the next step without purification.

Workup

  1. filtrationthe resulting orange precipitate was filtered
  2. washwashing the residue with chilled water
  3. customAfter drying under vacuum at 60° C., for 2 hours
  4. customthe brick-red solid was used in the next step without purification

Sources & evidence

ORD record
ord-ec8fbf85c3ab4e498eea5f7341e343fd
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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