3-Nitrobenzaldehyde → 2-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

HRID 54457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54457
[CH3:1]/[C:2](/[NH2:6])=[CH:3]\[C:4]#[N:5].[C:7]1(=[O:14])[CH2:12][CH2:11][CH2:10][C:9](=O)[CH2:8]1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O)([O-:17])=[O:16]>C(O)C>[C:4]([C:3]1[CH:21]([C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[C:12]2[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][C:11]=2[NH:6][C:2]=1[CH3:1])#[N:5]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 104341,3-CyclohexanedioneHCID 53247203-Aminocrotonitrile

Produkt 1

HCID 28632292-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrileAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-Aminocrotonitrile (0.91 g), 1,3-cyclohexanedione (1.25 g), and 3-nitrobenzaldehyde (1.70 g) were combined in ethanol (100 mL) and heated at reflux for 7 hours. Removal of solvent and chromatography (ethyl acetate) gave the title compound (2.40 g) as a yellow solid; mp 214°-216° C. NMR: 1.73-2.00 (m,2, CH2), 2.08 (s,3, CH3), 2.13-2.31 (m,2, CH2), 2.41-2.63 (m,2, CH2), 4.66 (s,1, CH), 7.61 (m,1, Ar), 7.68 (dd,1, J=7.7, 1.1 Ar), 7.98 (s,1, Ar), 8.07 (m,1, Ar), 9.66 (s,1, NH); MS: m/z=309(M). Analysis for C17H15N3O3 : Calculated: C, 66.01; H, 4.89; N, 13.58; Found: C, 65.78; H, 4.99; N, 13.45.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 7 hours
  3. customRemoval of solvent and chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4624caac74564864b5e1f5aa42eacd55
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622964

Notizen zur Reaktion

Wird geladen…