HCID 67431458, Verbindung → HCID 58459125, Verbindung

HRID 2036605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036605
[CH:1]1([NH:4][C:5]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[NH2:15][C:14]1[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

4

Edukt 1

HCID 67431458HCID 67431458, Verbindung

Produkt 1

HCID 58459125HCID 58459125, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(cyclopropylamino)-3-nitrobenzoate (1.1 g, 4.5 mmol) in MeOH (4 mL) was added palladium 10 wt % on carbon (0.24 g, 0.23 mmol) under N2. After flushing the flask with N2 several times, the solution was stirred under a H2 balloon for 6 h. LCMS showed the reaction was complete. After filtration of the reaction mixture and rinsing with MeOH, the filtrate was collected and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel column using 0-20% gradient of DCM-MeOH—NH4OH (9:1:0.05) in DCM as eluent gave methyl 3-amino-2-(cyclopropylamino)benzoate: LC-MS (ESI) m/z 207.1 [M+H]+.

Aufarbeitung

  1. customAfter flushing the flask with N2 several times
  2. filtrationAfter filtration of the reaction mixture
  3. washrinsing with MeOH
  4. customthe filtrate was collected
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography over silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-27cfdfd3609545469d2ff83e04f2d8bd
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575183B2

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