Stannous chloride dihydrate → Ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate

HRID 1067847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067847
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:6]2[CH3:21].O.O.[Sn](Cl)Cl.O.N>C(O)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[C:7]=2[N:6]([CH3:21])[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4]3)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 12896473Azane;hydrateHCID 21194161HCID 21194161, Verbindung

Produkt 1

HCID 21194433Ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylateAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4.10 g (10.9 mmol) of ethyl 4-chloro-1-methyl-7-(4-nitrophenoxy)-2-indolecarboxylate, 12.34 g (54.7 mmol) of tin (II) chloride dihydrate and 150 ml of ethanol was stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature, 28% ammonia water was added to render alkaline and the mixture was extracted with ethyl acetate. Insoluble matters were filtered off. The filtrate was washed with 5% sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2.70 g of ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. filtrationInsoluble matters were filtered off
  4. washThe filtrate was washed with 5% sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c0699f0ee82e4175ad2575ab7ce88a13
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248772B1

Notizen zur Reaktion

Wird geladen…