Acetyl chloride → 1-(6-Nitroindolin-1-yl)ethanone

HRID 252569

Reaktionsgleichung

Reaktionsgleichung von HRID 252569
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.[C:20](Cl)(=[O:22])[CH3:21]>C1COCC1>[C:20]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)(=[O:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 297576-Nitroindoline

Produkt 1

HCID 2585661-(6-Nitroindolin-1-yl)ethanoneAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Nitroindoline (3.0 g, 18.3 mmol) is dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at 0° C. Acetyl chloride (1.5 mL, 21 mmol) is added dropwise. The mixture is stirred at room temperature for 30 minutes. The mixture is partitioned between EtOAc and aqueous HCl. The organic layer is dried and concentrated to yield 1-acetyl-6-nitroindoline (3.8 g, 100%) as a yellow solid.

Aufarbeitung

  1. customat 0° C
  2. customThe mixture is partitioned between EtOAc and aqueous HCl
  3. customThe organic layer is dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81270818abb845a686811bb3a462e811
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868037B2

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