Methyl iodide → 1,4-Dimethylquinolinium iodide

HRID 1774070Notes

Reaction equation

HRID 1774070 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[I:12][CH3:13]>CO>[I-:12].[CH3:13][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 102854-Methylquinoline

Product 1

HCID 110769741,4-Dimethylquinolinium iodideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution mixture of lepidine (0.66 g, 4.65 mmol) and iodomethane (1.32 g, 9.3 mmol) in methanol (30 mL) was heated to reflux in a sealed tube overnight. After cooling to room temperature, methanol was removed under vacuum. Anhydrous acetone was added to the residue and filtered. The resulting solid was washed with acetone and dried to afford iodide 4 (1.1 g) as yellow solid in 83% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.35 (d, J=6 Hz, 1H), 8.54 (d, J=8.8 Hz, 1H), 8.49 (d, J=8.8 Hz, 1H), 8.27 (t, J=7.2 Hz, 1H), 8.07 (t, J=4.8 Hz, 1H), 8.05 (d, J=6 Hz, 1H), 4.57 (s, 3H), 3.00 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 158.1, 148.9, 137.6, 134.9, 129.6, 128.4, 126.8, 122.4, 119.5, 44.9, 19.6. MS (FAB) m/z Calcd for C11H12N+ 158.0 Found 158.2 [M]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a sealed tube overnight
  3. custommethanol was removed under vacuum
  4. additionAnhydrous acetone was added to the residue
  5. filtrationfiltered
  6. washThe resulting solid was washed with acetone
  7. customdried

Sources & evidence

ORD record
ord-affe69c5946744bb8297c02df99e0117
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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