Methyl iodide → 4-(5-Isopropoxy-2-methyl-4-nitro-phenyl)-1-methyl-pyridinium iodide

HRID 388561Notes

Reaction equation

[CH:1]([O:4][C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]([CH3:17])=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2].[I:21][CH3:22]>C1COCC1>[I-:21].[CH:1]([O:4][C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]([CH3:17])=[C:9]([C:11]2[CH:16]=[CH:15][N+:14]([CH3:22])=[CH:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

4-(5-Isopropoxy-2-methyl-4-nitro-phenyl)-pyridine (Example 7, Step 1, 217 mg, 0.797 mmol) is dissolved in anhydrous THF (9 mL). Iodomethane (0.10 mL, 1.61 mmol, 2 equiv.) is added and the reaction is stirred at 40° C. in a sealed tube for 2 days. The volatiles are removed under vacuum generating 4-(5-Isopropoxy-2-methyl-4-nitro-phenyl)-1-methyl-pyridinium iodide as a brown solid: ESMS m/z 287.1 (M+).

Workup

customThe volatiles are removed under vacuum

Sources & evidence

ORD record: ord-58051922a277400e96ae5809684f1aa8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377921B2

Reaction notes

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