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

HRID 2209520

Reaktionsgleichung

Reaktionsgleichung von HRID 2209520
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0c72ab7d2c094e37ab87e0b6f36effa9
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455253

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