Benzoyl Peroxide → 2-bromo-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

HRID 909

Reaktionsgleichung

Reaktionsgleichung von HRID 909
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]1=2.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>CN(C)C=O>[Br:32][C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][C:2](=[O:1])[C:3]=2[C:4]=1[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 153376324-Oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

Produkt 1

HCID 186965562-bromo-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acidAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (886 mg, 5 mmol) and catalytic benzoyl peroxide in N,N-dimethylformamide (5 mL) at 0° C. was added N-bromosuccinimide (1.869 g, 10.5 mmol)in four equal portions over 1 hour. The mixture was stirred an additional hour, then poured into ice water, the precipitate collected and rinsed with water then diethyl ether and dried. Purification on Silica gel (5% methyl alcohol in 1:1:1 dichloromethane/ethyl acetate/hexanes) gave 2-bromo-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (376 mg).

Aufarbeitung

  1. customthe precipitate collected
  2. washrinsed with water
  3. dry with materialdiethyl ether and dried
  4. customPurification on Silica gel (5% methyl alcohol in 1:1:1 dichloromethane/ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b9c7d82499f7455298f6c3c1fbf3995e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723462

Verknüpfte Notizen

Wird geladen…