Hydrochloric Acid → 337357-62-7

HRID 1582977ノート

反応式

HRID 1582977 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9801034Ethyl 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

生成物 1

HCID 10156040337357-62-7収率 50.6%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e2ad351257a64e23a77d88c1db7266a8
出典データセット
uspto-grants-2004_05
特許番号
US06740662B1

反応ノート

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