1-Iodopropane → 4-(3-Methoxy-4-nitrophenyl)-1-propylpyridinium iodide

HRID 419473Notes

Reaction equation

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

Participants

Conditions

Temperature: 102 °C

Procedure

To 4-[3-(methyloxy)-4-nitrophenyl]pyridine (5 g, 21.72 mmol) in 50 mL of pinacolone was added, 1-iodopropane (14.77 g, 86.87 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 (5.7 g, 14.24 mmol, 65%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (d, J=6.78 Hz, 2H), 8.64 (d, J=6.78 Hz, 2H), 8.09 (d, J=8.42 Hz, 1H), 7.90 (d, J=1.65 Hz, 1H), 7.75 (dd, J=8.42, 1.65 Hz, 1H), 4.59 (t, J=7.33 Hz, 2H), 4.06 (s, 3H), 1.91-2.01 (m, 2H), 0.90 (t, J=7.33 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-06ea7770fe8a4dfbadd7b5061b94a969
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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