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

HRID 2104397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104397
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[CH3:17].C([O-])(=O)C.[Na+]>ClCCCl>[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([C:29]=1[CH:14]=[O:15])=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[CH3:17]

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

Phosphorus oxychloride (2.0 mL) was added to N-methylformanilide (2.9 g), and after the mixture was stirred for 15 minutes, 1,2-dichloroethane (50 mL) and 5-chloroindole-2-carboxylic acid ethyl ester (4.0 g) were added thereto, followed by heating under reflux for 1 hour. The reaction mixture was poured into an aqueous solution (28 mL) of sodium acetate (14 g) under ice cooling, and the thus-obtained mixture was stirred for 18 hours. Insoluble matter was collected by filtration, and was sequentially washed with water and diethyl ether, to thereby give the title compound (3.56 g).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. stirringthe thus-obtained mixture was stirred for 18 hours
  4. filtrationInsoluble matter was collected by filtration
  5. washwas sequentially washed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1ab6c9c7a64a4bd69c583c9c181a6c61
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576135B2

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