Ethyl Acetate → 2-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile

HRID 131320

반응식

HRID 131320 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.F[C:13]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=1[C:15]#[N:16].O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=2[C:15]#[N:16])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 677694-Fluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 27745842-Fluoro-5-methylbenzonitrile

생성물 1

HCID 210934602-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile수율 45.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

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온도
55 °C

실험 절차

Combine 4-fluoro-2-nitro-phenylamine (2.9 g, 18.50 mmol), 2-fluoro-5-methyl-benzonitrile (2.5 g, 18.50 mmol) and lithium hydroxide monohydrate (2.4 g, 57.20 mmol) in methyl sulfoxide (DMSO, 40 ml). Heat the resulting mixture to 55° C. for 40 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Chromatograph the solid using flash chromatography and elute with mobile phase: 90% hexanes, 5% ethyl acetate, and 5% dichloromethane to obtain 2.267 g of the title compound (8.36 mmol, 45% yield) as an orange amorphous solid: Mass Spectrum (m/e): 272(M+1).

후처리

  1. temperatureCool the reaction mixture to ambient temperature
  2. filtrationFilter the resulting mixture
  3. customcollect the precipitate
  4. washelute with mobile phase

출처 및 근거

ORD 기록
ord-b3b2628025d8478b9fcf42782ca39456
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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