Hydrochloric Acid → Ethyl 4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-carboxylate

HRID 1582976

Reaktionsgleichung

Reaktionsgleichung von HRID 1582976
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:8]([NH:14][CH2:15][CH3:16])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=O.Cl[CH:21]([C:27]([O-:29])=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl>CN(C)C1C=CN=CC=1.ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[N:14]([CH2:15][CH3:16])[C:27](=[O:29])[C:21]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 110549023-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridineHCID 86592122Monoethyl chloromalonate

Produkt 1

HCID 12042351Ethyl 4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a 50 ml dichloroethane solution containing 7.5 g of 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine were added 5 ml of monoethyl chloromalonate and 6.5 g of 4-dimethylaminopyridine. The whole was stirred at room temperature for 30 minutes, and then further under heating at an oil bath temperature of 80° C. for 30 minutes. The reaction mixture was cooled to room temperature and, after adding 1M hydrochloric acid, extracted with chloroform. The organic layer was washed with saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate to chloroform-ethyl acetate) to obtain 7.10 g of ethyl 4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-carboxylate as colorless crystals.

Aufarbeitung

  1. temperaturefurther under heating at an oil bath temperature of 80° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate to chloroform-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-348f6d01df784eb98ea8f2c47d02a903
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740662B1

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