Methyl iodide → Quinolinium, 1,2-dimethyl-6-nitro-, iodide

HRID 2105104Notes

Reaction equation

HRID 2105104 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[I:15][CH3:16]>C(#N)C>[I-:15].[CH3:16][N+:3]1[C:4]2[C:9](=[CH:8][C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 691722-Methyl-6-nitroquinoline

Product 1

HCID 12252537Quinolinium, 1,2-dimethyl-6-nitro-, iodideYield 16.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methyl-6-nitroquinoline (0.5 g, 2.66 mmol) and iodomethane (1 ml, 16 mmol) were heated together in acetonitrile (10 ml) at reflux for 48 hrs. The mixture was cooled to room temperature and a grey material crystallised out of solution and was filtered off. This was shown to be starting material. The filtrate was diluted with ethyl acetate (200 ml) to give a yellow/green precipitate. The product was filtered off, washed with ethyl acetate and then dried under vacuum. The product was obtained as a yellow/green solid (147 mg, 16.8%).

Workup

  1. temperatureat reflux for 48 hrs
  2. customa grey material crystallised out of solution
  3. filtrationwas filtered off
  4. additionThe filtrate was diluted with ethyl acetate (200 ml)
  5. customto give a yellow/green precipitate
  6. filtrationThe product was filtered off
  7. washwashed with ethyl acetate
  8. customdried under vacuum

Sources & evidence

ORD record
ord-220eb2f3f15644d783f300d6b4e22aea
Source dataset
uspto-grants-2009_08
Patent number
US07579140B2

Reaction notes

Loading…