3-Nitrobenzaldehyde → 3-Acetyl-2-methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209528
[NH2:1][C:2]([CH3:7])=[CH:3][C:4](=[O:6])[CH3:5].[C:8]1(=[O:15])[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1.[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)([O-:18])=[O:17]>C(O)C>[C:4]([C:3]1[CH:22]([C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([N+:16]([O-:18])=[O:17])[CH:20]=2)[C:13]2[C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]=2[NH:1][C:2]=1[CH3:7])(=[O:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 104341,3-CyclohexanedioneHCID 1368734-Amino-3-penten-2-one

Produkt 1

HCID 149551863-Acetyl-2-methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinoloneAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Amino-3-penten-2-one (2.00 g), 1,3-cyclohexanedione (2.30 g), and 3-nitrobenzaldehyde (3.08 g) were combined in ethanol (180 mL) and heated at reflux for 5 hours. A yellow solid formed upon cooling to ambient temperature. The solid was purified by trituration with hot ethyl acetate/ethanol to yield the title compound (2.65 g) as a yellow solid; mp >250° C.; NMR: 1.67-1.97 (m,2, CH2), 2.13 (s,3, CH3), 2.22 (m,2, CH2), 2.35 (s,3, CH3), 2.47 (m,2, CH2), 5.11 (s,1, CH), 7.52 (m,1, Ar), 7.60 (d,1, J=7.7, Ar), 7.97 (m,2, Ar), 9.32 (s,1, NH); MS: m/z=326(M). Analysis for C18H18N2O4 : Calculated C, 66.25; H, 5.56; N, 8.58, Found: C, 65.99; H, 5.61; N, 8.40 .

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customA yellow solid formed
  4. customThe solid was purified by trituration with hot ethyl acetate/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4bc3e67b498840d0a5bb015f0b5196e6
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455253

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