2-Nitro-benzo[B]thiophene-3-carbonitrile → 2-Amino-1-benzothiophene-3-carbonitrile

HRID 1350485

反応式

HRID 1350485 の反応式
[N+:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[C:13]#[N:14])([O-])=O.[H][H]>ClCCCl.[Pd]>[NH2:1][C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[C:13]#[N:14]

参加物

5

反応物 2

HCID 210935092-Nitro-benzo[B]thiophene-3-carbonitrileHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 232735812-Amino-1-benzothiophene-3-carbonitrile収率 73%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 111,2-Dichloroethane溶媒

実験手順

Combine in a 500 mL schlenk flask, 2-nitro-benzo[b]thiophene-3-carbonitrile (5.8 g, 28.4 mmol) and Pd/C (3.0 g, 10% w/w, 2.84 mmol) in 1,2-dichloroethane (120 ml), the reaction mixture is charged with a balloon of hydrogen. After overnight stirring, release the hydrogen, remove the catalyst by filtration, and wash the catalyst by 1,2-dichloroethane several times. Concentrate down to a residue, which purified by flash chromatography on silica gel, gradient (100% hexane to 100% of Hexane:CH2Cl2:EtOAc=50:50:2.5), afford brownish solid 3.6 g of title compound (yield 73%). Mass spectrum: ES(+)(m/e): 175 (M+1); 1H NMR (300MHz, DMSO-d6, ppm): δ 7.81 (br, 2H), 7.65–7.62 (m, 1H), 7.28–7.24 (m, 2H), 7.11–7.01 (m, 1 H).

後処理

  1. customremove the catalyst
  2. filtrationby filtration
  3. washwash the catalyst by 1,2-dichloroethane several times
  4. concentrationConcentrate down to a residue, which
  5. custompurified by flash chromatography on silica gel, gradient (100% hexane to 100% of Hexane:CH2Cl2:EtOAc=50:50:2.5)

出典と根拠

ORDレコード
ord-2515c82699e644ab96891a0fb8b5b425
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

関連ノート

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