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

HRID 2425828Notes

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-fd606cdb1f5042209da1a9a3773798a9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968016B2

Reaction notes

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