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

HRID 1479589ノート

反応式

HRID 1479589 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4e1a6d3efbef415da6d5bf4d098750ae
出典データセット
uspto-grants-2016_08
特許番号
US09408907B2

反応ノート

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