Methanol → Tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate

HRID 1673359

Reaktionsgleichung

Reaktionsgleichung von HRID 1673359
CO.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:14]([N+:25]([O-])=O)[CH:13]=3)=[CH:11][C:6]=2[O:5][CH2:4]1>[C].[Pd].C(OCC)(=O)C>[NH2:25][C:14]1[CH:13]=[C:12]([C:10]2[CH:9]=[CH:8][C:7]3[O:3][CH2:4][O:5][C:6]=3[CH:11]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Komponenten

5

Edukt 2

HCID 887MethanolHCID 67342074Tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-nitrobenzoate

Produkt 1

HCID 67342168Tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.42 g of 10% palladium-carbon was added to a mixed solution of 14 mL of methanol and 14 mL of ethyl acetate containing 1.4 g of tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-nitrobenzoate and stirred under hydrogen atmosphere at room temperature for 2 hours. After insoluble were removed by filtration, the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=20:1] to obtain 0.52 g of tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate as pale red solid.

Aufarbeitung

  1. customAfter insoluble were removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=20:1]

Quellen und Nachweise

ORD-Eintrag
ord-21dfbbc2fa594164a90f99835772d944
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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