Pyrrolidine → 2,4-Dichloro-5-methoxyquinoline

HRID 1852279ノート

反応式

HRID 1852279 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 748913082,4-Dichloro-5-methoxyquinoline収率 43.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cd11744917a3425789a4df78410f56c4
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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