1,2-Dibromoethane → 1-(2-Bromoethyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276897

反応式

HRID 276897 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].[Br:16][CH2:17][CH2:18]Br>CN(C)C=O>[Br:16][CH2:17][CH2:18][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13]

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

生成物 1

HCID 226295731-(2-Bromoethyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one収率 34%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2a,3,4,5-Tetrahydrobenz[cd]indole-2(1H) -one (3.46 g, 20mmol) was dissolved in anhydrous N,N-dimethylformamide (20 ml). Thereto was added sodium hydride (0.8 g, 20 mmol), and the resulting solution was stirred at room temperature for 1 hour. The reaction solution was mixed with 1,2-dibromoethane (10 ml, 115 mmol) and again stirred for 1 hour. The reaction solution was extracted by adding 100 ml of ethyl acetate and 100 ml of water, and the resulting ethyl acetate layer was separated, washed with water and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was crystallized from a dimethylformamide-water mixture to obtain 1.9 g of the title compound (34% in yield).

後処理

  1. stirringagain stirred for 1 hour
  2. extractionThe reaction solution was extracted
  3. additionby adding 100 ml of ethyl acetate and 100 ml of water
  4. customthe resulting ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  8. customwas crystallized from a dimethylformamide-water mixture

出典と根拠

ORDレコード
ord-161e0de06b4448e39e039f9cdf33adef
出典データセット
uspto-grants-2002_03
特許番号
US06355642B1

関連ノート

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