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

HRID 45064노트

반응식

HRID 45064 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile수율 49.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8870ae512a4a46a39d80fff903dd4e74
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541432B2

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