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

HRID 54443ノート

反応式

HRID 54443 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 C16H15C12NO: 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-2d2b2e4a5a164d6b8ce7b6460355a93f
出典データセット
uspto-grants-1997_04
特許番号
US05622964

反応ノート

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