Hydrochloric Acid → Ethyl 4-amino-2-methoxy-5-nitrobenzoate

HRID 1465805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465805
C([NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:18][CH3:19])[CH:6]=1)(=O)C.Cl.[CH2:21](O)C>>[NH2:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH2:12][CH3:21])=[O:10])=[C:7]([O:18][CH3:19])[CH:6]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 77723Methyl 4-acetamido-2-methoxy-5-nitrobenzoate

Produkt 1

HCID 67231122Ethyl 4-amino-2-methoxy-5-nitrobenzoateAusbeute 91 %

Versuchsvorschrift

To a solution of methyl 4-acetamido-2-methoxy-5-nitrobenzoate (135 mg, 0.50 mmol) in ethanol 10 ml) was added concentrated hydrochloric acid (0.5 ml) dropwise and the mixture refluxed under nitrogen overnight. The reaction mixture was then cooled, the solvents removed and the residue purified by column chromatography (silica gel), eluting with 1:1 ethyl acetate/hexane to give ethyl 4-amino-2-methoxy-5-nitrobenzoate as a yellow solid (110 mg, 91%).

Aufarbeitung

  1. temperaturethe mixture refluxed under nitrogen overnight
  2. temperatureThe reaction mixture was then cooled
  3. customthe solvents removed
  4. customthe residue purified by column chromatography (silica gel)
  5. washeluting with 1:1 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-bff5e354b34a43b286885d9ce0ff467a
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999993B2

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