Acetic Acid → 3-Amino-5-(trifluoromethyl)benzonitrile

HRID 450213ノート

反応式

HRID 450213 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:7]#[N:8])([O-])=O.C(O)(=O)C.[Sn](Cl)Cl>CCO.O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)[C:7]#[N:8]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 24479Stannous ChlorideHCID 107274333-Cyano-5-nitrobenzotrifluoride

生成物 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile収率 49.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-nitro-5-(trifluoromethyl)benzonitrile (500 mg, 2.31 mmol) and acetic acid (6.62 mL, 116 mmol) in EtOH (10 mL) and water (10 mL) is added tin (II) chloride (2.61 g, 11.6 mmol) and the reaction mixture is heated at 80° C. for 6 h. The solvent is removed in vacuo and then the residue is portioned between DCM and 4 N HCl solution. The organic layer separated and then dried over anhydrous Na2SO4, filtered and concentrated. The residue is then separated via FCC (10-100% EtOAc/heptane) to give the compound as a yellow oil (213 mg, 49%). MS (ESI) m/z 185.3 (M+1).

後処理

  1. customThe solvent is removed in vacuo
  2. customThe organic layer separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is then separated via FCC (10-100% EtOAc/heptane)

出典と根拠

ORDレコード
ord-1cf6db249f2742feaaecedd44b610a42
出典データセット
uspto-grants-2013_07
特許番号
US08486954B2

反応ノート

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