N-bromobutanimide → 6-Bromo-1,2,3,4-tetrahydroquinolin-4-one

HRID 1296136ノート

反応式

HRID 1296136 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[Br:12]N1C(=O)CCC1=O>ClCCl>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][C:4]2=[O:11]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 1171582,3-dihydroquinolin-4(1H)-one

生成物 1

HCID 7594476-Bromo-1,2,3,4-tetrahydroquinolin-4-one収率 91.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−.

後処理

  1. customwas partitioned between aqueous sodium bicarbonate and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

出典と根拠

ORDレコード
ord-68a4bd1a5cac476c8895a8165f78e9d0
出典データセット
uspto-grants-2007_07
特許番号
US07244725B2

反応ノート

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