4-Chlorobenzaldehyde → 5-(4-Chlorophenyl)-1-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-4-propionylpyrrolidine-2,3-dione

HRID 873913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873913
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[O:20]=[C:21]([CH2:27][C:28](=[O:31])[CH2:29][CH3:30])[C:22](OCC)=[O:23]>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[N:1]([C:2]3[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=3)[C:22](=[O:23])[C:21](=[O:20])[CH:27]2[C:28](=[O:31])[CH2:29][CH3:30])=[CH:14][CH:13]=1

Komponenten

4

Edukt 3

HCID 77264-ChlorobenzaldehydeHCID 61590Ethyl-2,4-dioxohexanoateHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

Produkt 1

HCID 1177027665-(4-Chlorophenyl)-1-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-4-propionylpyrrolidine-2,3-dione

Versuchsvorschrift

The title compound was prepared in analogy to the procedure described in Step 57.1 using 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2), 4-chlorobenzaldehyde and ethyl 2,4-dioxohexanoate under reflux for 7 hr. The crude product was purified by silica gel chromatography (hexane/CH2Cl2/MeOH 40:60:10 to 0:60:10). tR: 0.82 min (LC-MS 2); ESI-MS: 387 [M+H]+ (LC-MS 2).

Aufarbeitung

  1. temperatureunder reflux for 7 hr
  2. customThe crude product was purified by silica gel chromatography (hexane/CH2Cl2/MeOH 40:60:10 to 0:60:10)

Quellen und Nachweise

ORD-Eintrag
ord-4a0ca84b940a4bb3915edc1f638780fc
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975417B2

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