Methyl 2-(4-cyano-2-nitrophenyl)acetate → 2-Oxindole-6-carbonitrile

HRID 552825

반응식

HRID 552825 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](OC)=[O:11])=[C:5]([N+:14]([O-])=O)[CH:4]=1)#[N:2]>CC(O)=O.[Fe]>[O:11]=[C:10]1[CH2:9][C:6]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[NH:14]1

참가 물질

4

반응물 1

HCID 23076960Methyl 2-(4-cyano-2-nitrophenyl)acetate

생성물 1

HCID 27733482-Oxindole-6-carbonitrile수율 56.6%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

Methyl (4-cyano-2-nitrophenyl)acetate (128 mg) was dissolved in AcOH (3.0 ml), followed by addition of iron powders (129 mg), and the reaction solution was stirred in an oil bath at 100° C. for 1.5 hours. It was concentrated to remove AcOH, followed by addition of EtOAc. The brown solid was separated by filtration, and the organic layer was washed with a 1M HCl solution and saturated brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5) to obtain to obtain 2-oxoindoline-6-carbonitrile (52.0 mg) as a pale yellow solid.

후처리

  1. concentrationIt was concentrated
  2. customto remove AcOH
  3. additionfollowed by addition of EtOAc
  4. customThe brown solid was separated by filtration
  5. washthe organic layer was washed with a 1M HCl solution and saturated brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5)
  9. customto obtain

출처 및 근거

ORD 기록
ord-541b4f61fcf84ca78a21f45b4ff0231a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951825B2

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