N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 2393442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393442
CN(C)[CH:3]=[CH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.[H][H]>C(O)C.[Pt]=O>[C:15]([NH:14][C:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][NH:11][C:10]2=[CH:9][N:8]=1)(=[O:17])[CH3:16]

Komponenten

5

Edukt 2

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamideAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine (6 g, 24 mmol) was hydrogenated over platinum oxide (0.5 g) in ethanol (120 mL) at 35 psi of hydrogen for 15 min. The catalyst was removed by filtration and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM to afford a purple solid. This was triturated with ether and the precipitate collected by filtration to give the title compound (1.4 g, 33%) as a beige solid. mp 220° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 2.07 (3H, s), 6.45 (1H, s), 7.55-7.57 (1H, m), 8.21 (1H, s), 8.46 (1H, s), 10.16 (1H, br s) and 11.42 (1H, br s).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM
  4. customto afford a purple solid
  5. customThis was triturated with ether
  6. filtrationthe precipitate collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-928529796528427aa2e02af5cdff0ed9
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807857

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