Hydrochloric Acid → 5-Bromo-7-nitroindoline

HRID 863437

Reaktionsgleichung

Reaktionsgleichung von HRID 863437
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:16])=[CH:10][C:11]=2[N+:13]([O-:15])=[O:14])[CH2:6][CH2:5]1)(=O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:16][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)[NH:4][CH2:5][CH2:6]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27292431-Acetyl-5-bromo-7-nitroindoline

Produkt 1

HCID 30189115-Bromo-7-nitroindolineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Acetyl-5-bromo-7-nitroindoline (5.05 g, 17.7 mmol) was added to a mixture comprising 6 ml of ethanol and 40 ml of 6N hydrochloric acid. The obtained mixture was heated under reflux for 3 hours, neutralized with sodium carbonate and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 4.13 g of 5-bromo-7-nitroindoline. This compound (301 mg, 1.24 mmol) was added to 10 ml of toluene, followed by the addition of 580 mg (2.55 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The obtained mixture was refluxed by heating under stirring for 3.5 hours and filtered to remove insolubles. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography to give 252 mg of the title compound.

Aufarbeitung

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a5cea643742e48a282769fa1d2297dfd
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721246

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