Ethyl 4-Cyano-2-nitrophenylacetate → 2-Oxindole-6-carbonitrile

HRID 1386341

反応式

HRID 1386341 の反応式
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:7]=1[N+:14]([O-])=O)C>C(O)(=O)C.[Fe]>[C:12]([C:9]1[CH:8]=[C:7]2[C:6]([CH2:5][C:4](=[O:3])[NH:14]2)=[CH:11][CH:10]=1)#[N:13]

参加物

4

反応物 1

HCID 21717235Ethyl 4-Cyano-2-nitrophenylacetate

生成物 1

HCID 27733482-Oxindole-6-carbonitrile収率 85.5%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

Iron powder (11.5 g, 205.2 mmol) was added to a saturated solution of ethyl(4-cyano-2-nitrophenyl)acetate (12 g, 51.3 mmol) in hot glacial acetic acid and the reaction mixture was stirred at 100° C. for 2 hours. The mixture was allowed to cool and poured into stirred ice water (1000 ml). The aqueous mixture was extracted with ethyl acetate, the extracts were combined, dried (MgSO4) and the solvent removed by evaporation. The solid residue was recrystallised from ethyl acetate to give 6-cyanooxindole (6.94 g, 85%).

後処理

  1. temperatureto cool
  2. additionpoured
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe solid residue was recrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-a8b936b9707b4e8d870f75c94a5c2f10
出典データセット
uspto-grants-2001_07
特許番号
US06265411B1

関連ノート

読み込み中…