Acetic Acid → Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

HRID 2164339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164339
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[N:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:23][O:22][C:20]([C:19]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][C:8]([O:10][CH3:11])=[CH:7][CH:6]=2)=[O:21]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13220377HCID 13220377, Verbindung

Produkt 1

HCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 1.7 kg (5.2 mole) of 5-methoxy-2-[(2-methoxy-2-oxoethyl)phenylamino]benzoic acid methyl ester, and 303 g (5.6 mole) of sodium methoxide in 10.0 l of anhydrous methanol was stirred at reflux for 90 minutes. The mixture was cooled to 20° C., filtered, and treated with 336 g (320 ml, 5.6 mole) of glacial acetic acid. The mixture was cooled in ice, and the precipitated crude product was filtered and washed with cold methanol followed by hexane. There was obtained 1267 g (82% yield) of the indole product of analytical purity, mp 114°-116° C.

Aufarbeitung

  1. temperatureat reflux for 90 minutes
  2. filtrationfiltered
  3. temperatureThe mixture was cooled in ice
  4. customthe precipitated crude product
  5. filtrationwas filtered
  6. washwashed with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-4416b813024e403ab708189c04a6a9a8
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04503236

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