Acetic Anhydride → Alphanitro-6-chloro-3-indoleacrylic acid methylester

HRID 616264

Reaktionsgleichung

Reaktionsgleichung von HRID 616264
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15]OCC.C(OC(=O)C)(=O)C>>[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 871116-ChloroindoleHCID 53395203alpha-Nitro-beta-ethoxyacrylic acid methylester

Produkt 1

HCID 53746644Alphanitro-6-chloro-3-indoleacrylic acid methylesterAusbeute 51 %

Versuchsvorschrift

A 4-l. battery jar was charged charged with 641 g (4.23 moles) of 6-chloroindole, 926 g (5.3 moles) of crude (ca. 85% pure) alpha-nitro-beta-ethoxy acrylic acid methylester and 475 g (4.65 moles) of acetic anhydride. The mixture was well stirred at room temperature for 45 hours to give a highly viscous suspension of an orange precipitate. 1.5 l of a mixture of benzene-ether-hexane 1:1:3 was added and the mixture stirred vigorously for 30 minutes. The product was collected by filtration, washed with 1:0 l of the same solvent mixture and dried at room temperature and 16 mmHg to constant weight to afford 600 g (51%) of product as orange crystals, m.p. 159°-160°.

Aufarbeitung

  1. additionbattery jar was charged
  2. customto give
  3. additiona highly viscous suspension of an orange precipitate
  4. stirringthe mixture stirred vigorously for 30 minutes
  5. filtrationThe product was collected by filtration
  6. washwashed with 1
  7. dry with material0 l of the same solvent mixture and dried at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-f7b508a4a85e4e0e81dadd7d423e3276
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073795

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