Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate → Methyl 3-amino-2-[(tert-butoxycarbonyl)amino]benzoate

HRID 1628376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628376
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:19][C:18]1[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Komponenten

4

Edukt 1

HCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

Produkt 1

HCID 53407727Methyl 3-amino-2-[(tert-butoxycarbonyl)amino]benzoateAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of methyl 2-[(tert-butoxycarbonyl)amino]-3-nitrobenzoate (103 g, 348 mmol) in methanol (800 mL) was added 10% palladium on carbon (50% wet; 10 g), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 5 hr. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residual solid was suspended in diisopropyl ether (300 mL), and the suspension was stirred at room temperature for 3 hr. The resulting solid was collected by filtration and washed with diisopropyl ether to give the title compound (42.0 g, 158 mmol, 45%). The mixture of the removed catalyst described above and a colorless solid (the title compound) was suspended in tetrahydrofuran (200 mL), and the suspension was stirred at room temperature for 30 minutes. The insoluble material (the catalyst) was removed by filtration, and the filtrate was concentrated in vacuo. The residual solid was suspended in diisopropyl ether (300 mL), and the suspension was refluxed for 30 min. The resulting solid was collected by filtration and washed with diisopropyl ether to give the title compound (33.9 g, 127 mmol, 36%) as a colorless solid. Total amount: 75.9 g, 285 mmol, 82%.

Aufarbeitung

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. stirringthe suspension was stirred at room temperature for 3 hr
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-59657ae4935f471ca403c66b2a6a9d7e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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