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

HRID 2425826Notes

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 methylpyridinium 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-b68d36ce859c434f9ac3dd04f45d6e37
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968016B2

Reaction notes

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