Nitric Acid → Ethyl 5-hydroxy-4-nitroindole-2-carboxylate

HRID 1791828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791828
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[N+:17]([O-])([OH:19])=[O:18]>ClCCl>[OH:2][C:3]1[C:4]([N+:17]([O-:19])=[O:18])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 20926Ethyl 5-methoxyindole-2-carboxylate

Produkt 1

HCID 22030612Ethyl 5-hydroxy-4-nitroindole-2-carboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-methoxyindole-2-carboxylate (8.15 g, 37.2 mmol), (prepared by the method described in Heterocycles Vol. 43, No. 2, p. 263–266), nitric acid adsorbed on silica gel (24 g) and dichloromethane (150 ml) was stirred at ambient temperature for 18 hours. The dichloromethane was removed in vacuo and the product washed off the silica with acetone. The acetone was evaporated in vacuo. The residue was treated again with nitric acid on silica (1 g) as above and the work up procedure repeated to give ethyl 5-hydroxy-4-nitroindole-2-carboxylate (5.8 g, 59%).

Aufarbeitung

  1. custom(prepared by the method
  2. customThe dichloromethane was removed in vacuo
  3. washthe product washed off the silica with acetone
  4. customThe acetone was evaporated in vacuo
  5. additionThe residue was treated again with nitric acid on silica (1 g) as above and the work up procedure

Quellen und Nachweise

ORD-Eintrag
ord-c0d5244af2d04652bf6b3bc60250d25d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074800B1

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