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

HRID 1386341

반응식

HRID 1386341 반응식
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]

참가 물질

4

반응물 1

HCID 21717235Ethyl 4-Cyano-2-nitrophenylacetate

생성물 1

HCID 27733482-Oxindole-6-carbonitrile수율 85.5%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a8b936b9707b4e8d870f75c94a5c2f10
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265411B1

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