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

HRID 552825

Reaktionsgleichung

Reaktionsgleichung von HRID 552825
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 27733482-Oxindole-6-carbonitrileAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-541b4f61fcf84ca78a21f45b4ff0231a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951825B2

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