1-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol → 1-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanone

HRID 1479589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479589
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]([OH:18])[CH3:17])=[CH:15][C:4]=2[N:3]=1>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:18])[CH3:17])=[CH:15][C:4]=2[N:3]=1

Komponenten

4

Edukt 1

HCID 582136971-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol

Produkt 1

HCID 582135271-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution 1-(5-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol (from Example 88) (1.0 eq.) and activated MnO2 (20 eq.) in DCM (0.1 M) was stirred at ambient temperature over night. The reaction mixture was diluted with DCM. The MnO2 was filtered off, and the filtrate was concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give 1-(5-aminobenzo[f][1,7]naphthyridin-8-yl)ethanone as a yellow solid: 1H NMR (acetone-d6): δ 9.11 (dd, 1H), 8.99 (dd, 1H), 8.56 (d, 1H), 8.20 (d, 1H), 7.94-7.88 (m, 2H), 6.90 (br s, 2H), 2.70 (s, 3H). LRMS [M+H]=238.1.

Aufarbeitung

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-4e1a6d3efbef415da6d5bf4d098750ae
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09408907B2

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