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 270696ノート

反応式

HRID 270696 の反応式
[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

参加物

6

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒HCID 11430Potassium Carbonate溶媒

反応条件

温度
75 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9e282313f2c9408c90b39426336e0c8f
出典データセット
uspto-grants-2008_11
特許番号
US07449582B2

反応ノート

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