3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one → 3-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

HRID 270696노트

반응식

HRID 270696 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:23])[N:14]([CH3:22])[C:15]2[C:20]([CH:21]=1)=[CH:19][N:18]=[CH:17][CH:16]=2>CCO.Cl.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][N:18]=[CH:17][CH:16]=3)[C:4]([Cl:11])=[CH:5][CH:6]=1

참가 물질

6

반응물 1

HCID 598338673-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

생성물 1

HCID 598338933-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one수율 93.15%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매HCID 11430Potassium Carbonate용매

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온도
75 °C

실험 절차

To a suspended solution of 3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one (1.55 g, 4.427 mmol) in EtOH (12 mL) is added a solution of Sn(II)Cl2 (3.80 g, 19.92 mmol) in HCl (con. 16 mL) at 75° C. After stirring for 30 minutes at 75° C., the mixture is diluted with EtOAc and neutralized with K2CO3 to a pH of 8. The organic layer is washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product. The crude product is purified by recrystallization with CH2Cl2/EtOAc/Hexane to give the titled intermediate as a solid (1.32 g, 93.15%).

후처리

  1. washThe organic layer is washed with saturated K2CO3, brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customThe crude product is purified by recrystallization with CH2Cl2/EtOAc/Hexane

출처 및 근거

ORD 기록
ord-9e282313f2c9408c90b39426336e0c8f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449582B2

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