3'-Ethoxy-3-nitrobiphenyl-4-acetic acid → 6-(3-Ethoxyphenyl)indolin-2-one

HRID 366589

Reaktionsgleichung

Reaktionsgleichung von HRID 366589
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17](O)=[O:18])=[C:12]([N+:20]([O-])=O)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]>C(O)(=O)C.[Fe]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:13]([CH2:16][C:17](=[O:18])[NH:20]3)=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 107806283'-Ethoxy-3-nitrobiphenyl-4-acetic acid

Produkt 1

HCID 106346366-(3-Ethoxyphenyl)indolin-2-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Iron powder (2.4 g) was added in one portion to 4.6 g of 3'-ethoxy-3-nitrobiphenyl-4-acetic acid in 40 mL of glacial acetic acid and refluxed for 2 hours. The reaction mixture was concentrated to dryness, treated repeatedly with ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1N hydrochloric acid and brine and then dried over anhydrous sodium sulfate and concentrated to give 3.5 g (91% yield) of 6-(3-ethoxyphenyl)-2-oxindole as a light brown solid.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additiontreated repeatedly with ethyl acetate
  4. filtrationfiltered
  5. customto remove the insolubles
  6. washThe filtrate was washed twice with 1N hydrochloric acid and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e88381fd25fc4bf6a40150b557ea8c8c
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130238

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