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

HRID 131320

反応式

HRID 131320 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b3b2628025d8478b9fcf42782ca39456
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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