Hydrochloric Acid → 1-(7-Amino-5-bromoindolin-1-yl)ethanone

HRID 4927

Reaktionsgleichung

Reaktionsgleichung von HRID 4927
C(O)C.[C:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([Br:19])=[CH:13][C:14]=2[N+:16]([O-])=O)[CH2:9][CH2:8]1)(=[O:6])[CH3:5].Cl>[Fe].O>[C:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([Br:19])=[CH:13][C:14]=2[NH2:16])[CH2:9][CH2:8]1)(=[O:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27292431-Acetyl-5-bromo-7-nitroindoline

Produkt 1

HCID 197113381-(7-Amino-5-bromoindolin-1-yl)ethanoneAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixed solution of ethanol (400 ml) and water (100 ml), were added N-acetyl-5-bromo-7-nitroindoline (133.1 g), iron powder (10 mesh; 75 g) and concentrated hydrochloric acid (5 ml), and the mixture was subjected to refluxing for 5 hours with vigorous stirring. The reaction mixture was filtered by suction while hot to remove insoluble matter, and then the filtrate thereof was concentrated and cooled on standing to give the intended compound 38.3 g (32.2%) as a brown needle crystal. M.P.: 154°-155° C.

Aufarbeitung

  1. temperatureto refluxing for 5 hours with vigorous stirring
  2. filtrationThe reaction mixture was filtered by suction while hot
  3. customto remove insoluble matter
  4. concentrationthe filtrate thereof was concentrated
  5. temperaturecooled

Quellen und Nachweise

ORD-Eintrag
ord-fa8c1a5973204abeab956b536c71aec8
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242912

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