Water → N-(5-cyanoindan-1-yl)propionic acid amide

HRID 2063500ノート

反応式

HRID 2063500 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:6][CH2:5]2.O.[CH3:17][N:18]1CCCC1=O>>[C:17]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:6][CH2:5]2)#[N:18]

参加物

4

反応物 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 59453384N-(5-bromoindan-1-yl)propionic acid amide

生成物 1

HCID 67160601N-(5-cyanoindan-1-yl)propionic acid amide収率 50%

実験手順

3.64 g of N-(5-bromoindan-1-yl)propionic acid amide were dissolved in 30 ml of 1-methyl-2-pyrrolidone. 1.8 g of cuprous cyanide were added to this solution followed by heating and refluxing for 2 hours. After returning the reaction solution to room temperature, the reaction solution was poured into water, and stirred for 1 hour. The resulting reaction mixture was filtered with CELITE and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine followed by drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=7/3 (volume ratio)) to obtain 1.46 g of the target compound. Yield: 50%

後処理

  1. temperatureby heating
  2. temperaturerefluxing for 2 hours
  3. customto room temperature
  4. customThe resulting reaction mixture
  5. filtrationwas filtered with CELITE
  6. extractionthe filtrate was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialby drying with anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=7/3 (volume ratio))

出典と根拠

ORDレコード
ord-dfb238a018714ae898dbdcacf4cafb21
出典データセット
uspto-grants-2012_10
特許番号
US08288393B2

反応ノート

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