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

HRID 1020279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020279
[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-a-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) d 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-14fb737b76bd4f919248cc1d33ecc5a8
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716319B2

Notizen zur Reaktion

Wird geladen…