Selenium Dioxide → 6-Fluoro-7-methoxyquinoline-2-carbaldehyde

HRID 338910ノート

反応式

HRID 338910 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[CH:6]=[CH:5]2.[Se](=O)=[O:16]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH:14]=[O:16])[CH:6]=[CH:5]2

参加物

4

反応物 2

HCID 24007Selenium DioxideHCID 867074426-Fluoro-7-methoxy-2-methylquinoline

生成物 1

HCID 867074436-Fluoro-7-methoxyquinoline-2-carbaldehyde収率 73.4%

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

To 6-fluoro-7-methoxy-2-methylquinoline (1.4 g, 7.3 mmol) in dioxane/water (10 ml/l mL) at ambient temperature was added selenium dioxide (0.97 g, 8.8 mmol) and the reaction was heated to reflux for 2-3 hours. After cooling, the reaction was filtered and the solids were washed with DCM. The filtrate was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-7-methoxyquinoline-2-carbaldehyde (1.1 g, 73% yield) as a tan solid.

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2-3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered
  5. washthe solids were washed with DCM
  6. dry with materialThe filtrate was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by reverse phase chromatography (SP4, 25M
  10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

出典と根拠

ORDレコード
ord-bea4fba9b6e94873b88fa45830637af6
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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