3-Nitrobenzaldehyde → 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 54438

반응식

HRID 54438 반응식
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[N+:21]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)([O-:23])=[O:22].C([O-])(=O)C.[NH4+:36]>C(O)C>[C:5]([CH:4]1[CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:14]2[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=2[NH:36][C:3]1([C:2]([F:11])([F:12])[F:1])[OH:10])([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

6

반응물 4

HCID 74493-NitrobenzaldehydeHCID 104341,3-CyclohexanedioneHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 517165Ammonium Acetate

생성물 1

HCID 199589053-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A stirred mixture of ethyl 4,4,4-trifluoroacetoacetate (6.00 mL), 1,3-cylohexanedione (4.65 g), 3-nitrobenzaldehyde (6.31 g), and ammonium acetate (6.57 g) in ethanol (350 mL) was heated at reflux for 4.5 hours. After removal of solvent the orange residue was treated diethyl ether, and the resulting precipitate was collected by filtration. The solid was triturated with hot diethyl ether, collected, and purified by chromatography (ethyl acetate) to yield 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl) -4,6,7,8-tetrahydro-5(1H)-quinolone (8.47 g) as a white solid. NMR: 0.85 (t,3, J=7.1, CH3), 1.86 (m,2, CH2), 2.07 (m,2, CH2), 2.27-2.44 (m, 1, CH2), 2.57-2.72 (m, 1, CH2), 2.75 (d,1, J=11.9, CH), 3.83 (m,2, CH2), 4.07 (d,1, J=11.4, CH), 7.30 (s,1, OH), 7.50 (m, 1, Ar), 7.57 (m,1, Ar), 7.87 (m,1, Ar), 8.01 (m,1, Ar), 8.16 (s,1, NH); MS: m/z=428(M).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customAfter removal of solvent the orange residue
  4. additionwas treated diethyl ether
  5. filtrationthe resulting precipitate was collected by filtration
  6. customThe solid was triturated with hot diethyl ether
  7. customcollected
  8. custompurified by chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-caca7e7098d74a6ca35b9b41b45a1e7d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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