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

HRID 54443노트

반응식

HRID 54443 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2d2b2e4a5a164d6b8ce7b6460355a93f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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