1-Iodopropane → 4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide

HRID 419521Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[I:19][CH2:20][CH2:21][CH3:22]>CC(=O)C(C)(C)C.CC(C)=O>[I-:19].[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][N+:16]([CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 102 °C

Procedure

To 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]pyridine (750 mg, 3.07 mmol) in 15 mL of pinacolone was added, 1-iodopropane (2.1 g, 2.66 mmol). The mixture was heated to 102° C. for 24 h. The mixture was cooled and diluted with acetone. The resulting slurry was filtered and washed with acetone. The product was dried under vacuum to give the title compound of step B (1.1 g, 14.24 mmol, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.19 (d, J=6.78 Hz, 2H), 8.30 (d, J=6.59 Hz, 2H), 7.94 (s, 1H), 7.37 (s, 1H), 4.61 (t, J=7.23 Hz, 2H), 3.93 (s, 3H), 2.26 (s, 3H), 1.92-2.02 (m, 2H), 0.92 (t, J=7.42 Hz, 3H).

Workup

temperatureThe mixture was cooled
filtrationThe resulting slurry was filtered
washwashed with acetone
customThe product was dried under vacuum

Sources & evidence

ORD record: ord-0bba2445645f4b5796e7665ba3fbb82c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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