7-Bromo-1-Chloroisoquinoline → 7-Bromo-1-butylisoquinoline

HRID 349055

反応式

HRID 349055 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[CH2:13]([Mg]Cl)[CH2:14][CH2:15][CH3:16]>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418265HCID 178418265、化合物

生成物 1

HCID 210859957-Bromo-1-butylisoquinoline収率 24.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a refluxing solution of 7-bromo-1-chloroisoquinoline (4.85 g, 23.28 mmol) in diethyl ether (75 mL) was added butylmagnesium chloride (17.8 mL, 2.0 M ether, 35.6 mmol) and the reaction maintained at reflux for 2 h. The reaction mixture was cooled to room temperature, carefully diluted with an equal volume of ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an brown oil. Purification by flash column chromatography (silica, 1–10% ether/hexanes) gave the desired 7-bromo-1-butylisoquinoline (1.50 g): ESI MS m/z 264 [M+H]+.

後処理

  1. temperaturethe reaction maintained
  2. temperatureat reflux for 2 h
  3. washwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an brown oil
  8. customPurification by flash column chromatography (silica, 1–10% ether/hexanes)

出典と根拠

ORDレコード
ord-08c206c12c7d441bac3b2682a3e116dc
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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