1,3-Cyclohexanedione → 4-(3,4-Dichlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209526ノート

反応式

HRID 2209526 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14]1(=[O:21])[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]1.C([O-])(=O)C.[NH4+:26]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:15]3[C:14](=[O:21])[CH2:19][CH2:18][CH2:17][C:16]=3[NH:26][C:11]([CH3:12])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 104341,3-CyclohexanedioneHCID 3265634-(3,4-Dichlorophenyl)-3-buten-2-oneHCID 517165Ammonium Acetate

生成物 1

HCID 199589084-(3,4-Dichlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone収率 36.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-(3,4-dichlorophenyl)but-1-en-3-one (5.0 g), 1,3-cyclohexanedione (2.71 g), ammonium acetate (2.70 g) and ethanol (75 mL) was heated at reflux for ten hours. The reaction was worked up as described in Example 8, and recrystallization from ethyl acetate-hexane yielded the title compound (2.6 g) as an off-white solid, mp 199°-201° C.; NMR: 1.74 (s,3, CH3), 1.84-1.88 (m,2, CH2), 2.14-2.19 (m,2, CH2), 2.41-2.46 (m,2, CH2), 4.42 (d,1, J=4.7, CH), 4.59 (d,1, J=4.7, CH), 7.12 (dd,1, J=8.3,2.0, Ar), 7.31 (d,1, J=2.0, Ar), 7.48 (d,1, J=8.3, Ar), 8.55 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C16H15Cl2NO: Calculated C, 62.35; H, 4.91; N, 4.54; Found: C, 62.03; H, 5.09; N, 4.44.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for ten hours
  3. customas described in Example 8, and recrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-b0acd04057484f908f00221d3c355e8c
出典データセット
uspto-grants-1995_10
特許番号
US05455253

反応ノート

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