1,3-Cyclohexanedione → ethyl 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate

HRID 2167309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167309
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[CH3:9][CH2:10][O:11][C:12](/[C:14](/[C:22]#[N:23])=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C(O)C>[NH2:23][C:22]1[O:7][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]=2[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]=1[C:12]([O:11][CH2:10][CH3:9])=[O:13]

Komponenten

4

Edukt 2

HCID 104341,3-CyclohexanedioneHCID 668187alpha-Cyanocinnamic acid ethyl ester

Produkt 1

HCID 2767703ethyl 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1,3-cyclohexane dione (0.56 g, 5.0 mmole) in hot ethanol (10 ml) was added ethyl trans-α-cyanocinnamate (1.0 g, 5.0 mmole) and the mixture heated at reflux for 18 h. The mixture was cooled to room temperature, filtered and washed with ethanol to provide the desired product (1.30 g, 83%) as a white powder. 1H NMR (400 MHz; CDCl3) δ 7.29-7.0 (m, 5H); 6.2 (bs, 2H); 4.72 (s, 1H); 4.09-3.96 (m, 2H); 2.64-2.48 (m, 2H); 2.40-2.26 (m, 2H); 2.06-1.88 (m, 2H); 1.14 (t, 3H, J=7.4 Hz). LC MS shows MH+ at 314.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 h
  3. filtrationfiltered
  4. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f93109a9f5ae42d498867ff988a36e8c
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045428B2

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