2,5-Dichloronitrobenzene → 1-(4-Chloro-2-nitrophenyl)indoline

HRID 3997

Reaktionsgleichung

Reaktionsgleichung von HRID 3997
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>CN(C)C=O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Komponenten

4

Edukt 2

HCID 69772,5-DichloronitrobenzeneHCID 10328Indoline

Produkt 1

HCID 138233221-(4-Chloro-2-nitrophenyl)indoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 38.4 g (0.20 mole) of 1,4-dichloro-2-nitrobenzene and 59.6 g (0.50 mole) of indoline in 400 ml of dimethylformamide (DMF) was heated under nitrogen at 140°-145° C. overnight (23 hours). The DMF solvent was then removed in vacuo and the residue was dissolved in 500 ml of dichloromethane. This solution was extracted with H2O, with dilute hydrochloric acid, with brine, then dried over Na2SO4 and concentrated to an oil. This was adsorbed on a tall chromatography column containing 1.5 kg of silica gel packed in toluene. Elution with toluene brought forth 22.1 g (40% overall yield) of product, which crystallized. A small portion was recrystallized from hexane to afford 1-(4-chloro-2-nitrophenyl)indoline, m.p. 97°-99° C.

Aufarbeitung

  1. customThe DMF solvent was then removed in vacuo
  2. dissolutionthe residue was dissolved in 500 ml of dichloromethane
  3. extractionThis solution was extracted with H2O, with dilute hydrochloric acid, with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. additioncontaining 1.5 kg of silica gel
  7. washElution with toluene
  8. custom22.1 g (40% overall yield) of product, which
  9. customcrystallized
  10. customA small portion was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-b8580d0aef4048cc80058e48c5dcb458
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723007

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