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

HRID 1014189ノート

反応式

HRID 1014189 の反応式
[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]

参加物

4

反応物 2

HCID 336431-IodopropaneHCID 137288334-(3-Methoxy-4-nitrophenyl)pyridine

生成物 1

HCID 666496524-(3-Methoxy-4-nitrophenyl)-1-propylpyridinium iodide

試薬・触媒・溶媒 1

HCID 6416Pinacolone溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e730af83f38e4960bf25e80061ad1f54
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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