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

HRID 1582976Notes

Reaction equation

HRID 1582976 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-348f6d01df784eb98ea8f2c47d02a903
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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