Acetic Acid → 8-Bromo-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52462

Reaktionsgleichung

Reaktionsgleichung von HRID 52462
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[N:7]([C:14]([C:16]([O:18]CC)=O)=[O:15])[CH2:6][CH2:5]2.O.C(O)(=O)C>C1COCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:5][CH2:6][N:7]3[C:14](=[O:15])[C:16](=[O:18])[NH:11][C:9]([CH:10]=1)=[C:8]23

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 962WaterHCID 100202975-bromo-7-nitro-N-ethoxalylindoline

Produkt 1

HCID 117777348-Bromo-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dioneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10313229titanium(III) trichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-7-nitro-N-ethoxalylindoline (2.0 g, 5.83 mmol) in a mixture of THF (50 mL), water (10 mL), and acetic acid (10 mL) was added aqueous 20% titanium trichloride (31 mL, 40.8 mmol) and the mixture was stirred for 4 h at room temperature. The precipitates formed were collected by filtration, washed with diluted aqueous hydrochloric acid and then distilled water, and dried in vacuo to give 772 mg of the title compound (50%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ11.91 (bs, 1H), 7.21 (d, 1H, J=1 Hz), 7.02 (d, 1H, J=1 Hz), 4.22 (t, 2H, J=7 Hz), 3.32 (t, 2H, J=7 Hz).

Aufarbeitung

  1. customThe precipitates formed
  2. filtrationwere collected by filtration
  3. washwashed with diluted aqueous hydrochloric acid
  4. dry with materialdistilled water, and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8bb1305d46414b1fb4b3af0acb2da657
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616586

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