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

HRID 1014189Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

n-Propyliodide (200 mL, 2.05 mol) was added to a solution of 4-(3-methoxy-4-nitrophenyl)pyridine (25.0 g, 109 mmol) in pinacolone (500 mL). The reaction was fitted with a reflux condenser, stirred, and heated at 100° C. for 12 h. A light brown suspension was observed. An aliquot (˜2.0 mL) was taken out from the reaction mixture, concentrated, and analyzed by 1H NMR which revealed the formation of the alkylated product and the absence of starting material. The reaction was cooled; the solids were filtered off and rinsed once with cold (0° C.) acetone to afford 4-(3-methoxy-4-nitrophenyl)-1-propylpyridinium iodide as a light brown residue (29.0 g, 67% yield). 1 H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.3 Hz, 3 H), 1.99 (dt, J=7.3, 7.3 Hz, 2 H), 4.08 (s, 3 H), 4.59 (t, J=7.1 Hz, 2 H), 7.78 (dd, J=1.5, 8.4 Hz, 1H), 7.92 (d, J=1.5 Hz, 1 H), 8.13 (d, J=8.4 Hz, 1 H), 8.65 (d, J=7.0 Hz, 2 H), 9.22 (d, J=6.6 Hz, 2 H).

Workup

customThe reaction was fitted with a reflux condenser
concentrationconcentrated
temperatureThe reaction was cooled
filtrationthe solids were filtered off
washrinsed once with cold (0° C.) acetone

Sources & evidence

ORD record: ord-e730af83f38e4960bf25e80061ad1f54
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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