Hydrochloric Acid → 6-(4-chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 1799175ノート

反応式

HRID 1799175 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[C:15]4[C:20](=[N:21][CH:22]=3)[N:19]([CH3:23])[C:18](=[O:24])[CH:17]=[C:16]4[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)OCC[O:9]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:13]2[CH:14]=[C:15]3[C:20](=[N:21][CH:22]=2)[N:19]([CH3:23])[C:18](=[O:24])[CH:17]=[C:16]3[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)=[O:9])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 593347506-(2-(4-chlorophenyl)-1,3-dioxolan-2-yl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 593346916-(4-chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one収率 92.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

To a solution compound H (0.3 g, 0.67 mmol) in dioxane (5 mL) was added 6 N HCl (0.5 mL) at 0° C. The mixture was heated at 70° C. for 1.5 h and cooled to RT. Dioxane was removed under reduced pressure; the reaction mixture was neutralized with saturated NaHCO3 solution and extracted with EtOAc (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography to obtain 0.25 g (92%) of compound I as off-white solid.

後処理

  1. temperaturecooled to RT
  2. customDioxane was removed under reduced pressure
  3. extractionextracted with EtOAc (25 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-71e86fc1eaad492eb7b873129b447251
出典データセット
uspto-grants-2013_01
特許番号
US08343996B2

反応ノート

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