(2-Chloro-5-nitrophenyl)acetonitrile → 2-(5-Amino-2-chlorophenyl)acetonitrile

HRID 270711

反応式

HRID 270711 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH2:11][C:12]#[N:13]>CCO.Cl.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:11][C:12]#[N:13])[CH:4]=1

参加物

6

反応物 1

HCID 53396322(2-Chloro-5-nitrophenyl)acetonitrile

生成物 1

HCID 533963332-(5-Amino-2-chlorophenyl)acetonitrile収率 91.2%

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 (2-Chloro-5-nitro-phenyl)-acetonitrile (4.0 g, 20.0 mmol) in EtOH (10 mL) is added a solution of Sn(II)Cl2 (15.36 g, 81.0 mmol) in concentrated HCl (14 mL) at 75° C. After the mixture is stirred for 30 minutes at 75° C., the mixture is diluted with EtOAc and neutralized with K2CO3 until a pH of 8 is achieved. The organic layer is washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product, which is purified by recrystallization with CH2Cl2/EtOAc/Hexane to give the title intermediate as a solid (3.04 g, 89.7%).

後処理

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

出典と根拠

ORDレコード
ord-ae2d1c4a708a4d2f8e3b0c0fc887c5e7
出典データセット
uspto-grants-2008_11
特許番号
US07449582B2

関連ノート

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