Methyl iodide → 4-(4-Methoxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

HRID 1169525Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:17])=[C:5]([CH3:18])[CH:4]=1.[I:19][CH3:20]>C(Cl)Cl>[I-:19].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N+:13]([CH3:20])=[CH:12][C:11]=2[CH3:17])=[C:7]([CH3:9])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4 (0.241 g, 1.00 mmol) in dry CH2Cl2 (5 mL) was added dropwise iodomethane (0.32 mL, 0.729 g, 5.10 mmol) at room temperature under N2. The reaction mixture was then refluxed at 60° C. under N2 for 1 h. After cooling to room temperature, the mixture was concentrated in vacuo to give the corresponding methyl pyridinium iodide salt as an analytically pure yellow solid (0.382 g, 99.8%). mp 220-221° C.; 1H NMR (400 MHz, CD2Cl2): δ 9.079 (s, 2H), 6.751 (s, 2H), 4.579 (s, 3H), 3.881 (s, 3H), 2.135 (s, 6H), 1.854 (s, 6H); 13C NMR (100 MHz, CD2Cl2): δ 160.512, 159.866, 143.124, 138.802, 135.527, 125.927, 114.217, 55.692, 48.686, 20.188, 17.331; Anal. Calcd. For C17H22INO: C, 53.27; H, 5.79; N, 3.65. Found: C, 53.15; H, 5.79; N, 3.57.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-9abd44695a1e4f5e9c10b0134b0cf9e7
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07824582B2

Reaction notes

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