p-Toluenesulfonic acid monohydrate → Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

HRID 1696346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696346
[N+:1]([C:4]1[C:12]2[N:11]([CH2:13][C:14](OC)=[O:15])[C:10](=[O:18])[N:9]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pd]>[O:18]=[C:10]1[N:11]2[CH2:13][C:14](=[O:15])[NH:1][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([C:12]=32)[N:9]1[CH2:19][C:20]([O:22][CH3:23])=[O:21]

Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66636623Dimethyl 2,2'-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate

Produkt 1

HCID 86629734Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of dimethyl 2,2′-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate from Step B (270 mg, 0.84 mmol) and 10% Pd/C (50 mg) in MeOH (10 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm). After 2 h, the reaction was filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in toluene (3 mL) and p-toluenesulfonic acid monohydrate (2 mg, 0.011 mmol) was added. The mixture was heated at reflux for 30 min and then concentrated in vacuo to give the title compound. MS: m/z=262 (M+1).

Aufarbeitung

  1. filtrationthe reaction was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude solid was dissolved in toluene (3 mL)
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 30 min
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dc1129cab0d44e12bfa788d7b326d510
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163752B2

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