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

HRID 1799175노트

반응식

HRID 1799175 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71e86fc1eaad492eb7b873129b447251
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343996B2

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