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

HRID 1582976노트

반응식

HRID 1582976 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-348f6d01df784eb98ea8f2c47d02a903
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740662B1

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