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

HRID 1014189노트

반응식

HRID 1014189 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6416Pinacolone용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e730af83f38e4960bf25e80061ad1f54
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

반응 노트

불러오는 중…