Pyrrolidine → 2,4-Dichloro-5-methoxyquinoline

HRID 1852279노트

반응식

HRID 1852279 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6](OC)=[CH:7][CH:8]=2)[N:3]=1.N1CCCC1.CCN(C(C)C)C(C)C.[O:29]1CCOC[CH2:30]1>O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:29][CH3:30])[N:3]=1

참가 물질

6

반응물 4

HCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 228320542,4-Dichloro-7-methoxyquinoline

생성물 1

HCID 748913082,4-Dichloro-5-methoxyquinoline수율 43.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

To a solution of 2,4-dichloro-7-methoxyquinoline (0.1 g, 0.43 mmol) in 1,4-Dioxane (10 ml) was added pyrrolidine (0.3 g, 0.43 mmol) followed by DIPEA (0.11 g, 0.87 mmol) at room temperature. The reaction mass was heated at 140° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (50 mg, 43.4%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.86-7.83 (d, J=12 Hz, 1H), 7.06 (s, 1H), 6.88-6.85 (d, J=12 Hz, 1H), 6.67 (s, 1H), 3.91 (s, 3H), 3.58 (t, J=8 Hz, 4H), 2.03 (t, J=6 Hz, 1H); MS: MS m/z 263.1 (M++1).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customto get crude compound
  5. customThe crude compound was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-cd11744917a3425789a4df78410f56c4
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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