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3-Bromo-5-ethoxy-4-hydroxybenzaldehyde → 4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-3-nitro-7-propyl-4,6,7,8-tetra-hydro-1H-quinolin-5-one

HRID 909388
ノート
印刷プレビュー

反応式

HRID 909388 の反応式
[CH3:1][C:2]([NH2:7])=[CH:3][N+:4]([O-:6])=[O:5].[CH2:8]([CH:11]1[CH2:16][C:15](=[O:17])[CH2:14][C:13](=O)[CH2:12]1)[CH2:9][CH3:10].[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:29][CH2:30][CH3:31])[C:27]=1[OH:28])[CH:23]=O>C(O)C>[Br:19][C:20]1[CH:21]=[C:22]([CH:23]2[C:14]3[C:15](=[O:17])[CH2:16][CH:11]([CH2:8][CH2:9][CH3:10])[CH2:12][C:13]=3[NH:7][C:2]([CH3:1])=[C:3]2[N+:4]([O-:6])=[O:5])[CH:25]=[C:26]([O:29][CH2:30][CH3:31])[C:27]=1[OH:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 27372245-Propylcyclohexane-1,3-dioneHCID 714047121-Nitroprop-1-en-2-amine

生成物 1

HCID 674109084-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-3-nitro-7-propyl-4,6,7,8-tetra-hydro-1H-quinolin-5-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-methyl-2-nitro-vinylamine (1 g), 5-propylcyclohexane-1,3-dione (1.61 g) and 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (2.57 g) in ethanol (50 ml) was stirred at reflux for 17 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane. A precipitate formed, which was collected by filtration. The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent. Yield: 2.8 g. MS-ESI: [M+H]+=465.0/467.0

後処理

  1. temperatureat reflux for 17 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customA precipitate formed
  5. filtrationwhich was collected by filtration
  6. customThe solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent

出典と根拠

ORDレコード
ord-6614b13ee94444c9a27fb18c52faee20
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017782B2

反応ノート

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