Hydrochloric Acid → HCID 21083236, Verbindung

HRID 347634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347634
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 21083245HCID 21083245, Verbindung

Produkt 1

HCID 21083236HCID 21083236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a degassed solution of the cyanobenzoyl benzaz pin from Example 1A (1.50 g, 5.43 mmol) in methanol (50 ml) were added concentrated hydrochloric acid (1.4 ml, 16.2 mmol) and 10% palladium-on-carbon (1.15 g). Hydrogen gas was bubbled through the mixture for 5 h at room temperature. The catalyst was removed by filtration through a pad of celite and the filtrate was evaporated in vacuo. The residue was partitioned between EtOAc and water. The aqueous layer was basified by addition of saturated sodium bicarbonate solution and extracted with dichloromethane (2 times). The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to give a white solid; yield 1.12 g (74%).

Aufarbeitung

  1. customHydrogen gas was bubbled through the mixture for 5 h at room temperature
  2. customThe catalyst was removed by filtration through a pad of celite
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was partitioned between EtOAc and water
  5. additionThe aqueous layer was basified by addition of saturated sodium bicarbonate solution
  6. extractionextracted with dichloromethane (2 times)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-89d3f1d81801481fb78baf442d8fbb74
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176195B2

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