Phosphorus oxychloride → ethyl 5-chloro-3-formyl-1H-indole-2-carboxylate

HRID 1392764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392764
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2.C([O-])(=O)C.[Na+]>ClCCCl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:20]2[CH:14]=[O:15]

Komponenten

6

Edukt 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 517045Sodium Acetate

Produkt 1

HCID 4410568ethyl 5-chloro-3-formyl-1H-indole-2-carboxylateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

After phosphorus oxychloride (2.0 ml) was added to N-methylformanilide (2.9 g), and the mixture was stirred for 15 minutes, 1,2-dichloroethane (50 ml) and ethyl 5-chloroindole-2-carboxylate (4.0 g) were added, and the resultant mixture was heated under reflux for 1 hour. The reaction mixture was poured into an aqueous solution (28 ml) of sodium acetate (14 g) under ice cooling. After stirring for 18 hours, insoluble matter was collected by filtration. This product was successively washed with water and diethyl ether to obtain the title compound (3.56 g).

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. stirringAfter stirring for 18 hours
  3. filtrationinsoluble matter was collected by filtration
  4. washThis product was successively washed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-dfe73ba6ac7b4da7a3dcddd38547c7eb
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342014B2

Notizen zur Reaktion

Wird geladen…