Hydrochloric Acid → 337357-62-7

HRID 1582977Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[N:15][C:16]([CH3:20])=[CH:17][CH:18]=3)[N:13]([CH2:21][CH3:22])[C:12](=[O:23])[C:11]=2[CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:7]=[CH:8][CH:9]=1.Cl>C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[N:15][C:16]([CH3:20])=[CH:17][CH:18]=3)[N:13]([CH2:21][CH3:22])[C:12](=[O:23])[C:11]=2[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 15 ml portion of a 1M sodium hydroxide aqueous solution was added to 15 ml of a THF-methanol (1:1) solution containing 2.70 g of ethyl 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate, followed by stirring under heating at an oil bath temperature of 80° C. for 2 hours. After cooling to room temperature, the whole was adjusted to pH 3 with 1M hydrochloric acid and extracted with ethyl acetate. 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 (chloroform-methanol) and further recrystallized from diisopropyl ether-ethyl acetate to obtain 1.27 g of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as colorless crystals.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
customthe solvent was evaporated
customThe resulting residue was purified by a silica gel column chromatography (chloroform-methanol)
customfurther recrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record: ord-e2ad351257a64e23a77d88c1db7266a8
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740662B1

Reaction notes

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