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

HRID 1801416Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring solution of 6 (0.113 g, 0.500 mmol) in anhydrous methanol (10 mL) was added dropwise iodomethane (0.5 mL, 0.660 g, 2.75 mmol) at room temperature under N2. The reaction mixture was then stirred at 60° C. under N2 overnight. After cooling to room temperature, the mixture was concentrated in vacuo to give the corresponding methylpyridinium iodide salt as an analytically pure yellow solid (0.184 g, 99.4%). mp 257-258° C.; 1H NMR (500 MHz, DMSO-d6): δ 9.562 (s, 1H), 8.898 (s, 2H), 6.645 (s, 2H), 4.295 (s, 3H), 2.015 (s, 6H), 1.760 (s, 6H); 13C NMR (125 MHz, DMSO-d6): δ 157.588, 157.448, 143.158, 136.942, 134.675, 124.179, 114.988, 47.297, 19.162, 16.527; MS (ESI): m/z 242.4 [(M−I)+, 100]; Anal. Calcd. For C16H20INO.H2O: C, 49.62; H, 5.73; N, 3.62; I, 32.77. Found: C, 50.08; H, 5.52; N, 3.65; I, 33.49.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-392b6abecc6c49879ccc2b39e4ce59f7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349222B2

Reaction notes

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