N-(4-Chlorophenyl)acetamide → 2-[4-(4-Chloroanilino)-phenyl]propionic acid

HRID 1576580ノート

反応式

HRID 1576580 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.CC([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=O.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 10871N-(4-Chlorophenyl)acetamideHCID 11430Potassium CarbonateHCID 10589545Methyl 2-(4-iodophenyl)propanoate

生成物 1

HCID 215114592-[4-(4-Chloroanilino)-phenyl]propionic acid

試薬・触媒・溶媒 1

HCID 23978Copper触媒

実験手順

Methyl 2-(4-iodophenyl)propionate (2 g.), acet-p-chloroanilide (1.17 g.), potassium carbonate (0.62 g.) and copper powder (0.1 g.) were heated at 165°C. for 7.5 hours. The cooled solid was triturated with methylene chloride, filtered, and the filtrate evaporated to dryness. The residue was refluxed for 1.5 hours with ethanol (7 ml.) and 2.5N sodium hydroxide (14 ml.); ethanol was distilled in vacuo and the residue diluted with water, washed with ether and acidified with dilute hydrochloric acid. The resulting oil was isolated in ether and evaporated to dryness. The resulting gum was purified by preparative layer chromatography using 5% acetic acid/petroleum ether b.p. 62°-68°C. and eluting with ethyl acetate; recrystallization from benzene/petroleum ether b.p. 62°-68°C. and from petroleum ether b.p. 80°-100°C. gave 2-[4-(4-chloroanilino)-phenyl]propionic acid, m.p. 106-109°C.

後処理

  1. customThe cooled solid was triturated with methylene chloride
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. temperatureThe residue was refluxed for 1.5 hours with ethanol (7 ml.) and 2.5N sodium hydroxide (14 ml.)
  5. distillationethanol was distilled in vacuo
  6. additionthe residue diluted with water
  7. washwashed with ether
  8. customThe resulting oil was isolated in ether
  9. customevaporated to dryness
  10. customThe resulting gum was purified by preparative layer chromatography
  11. washeluting with ethyl acetate
  12. customrecrystallization from benzene/petroleum ether b.p. 62°-68°C.

出典と根拠

ORDレコード
ord-1f49bad261de4cf89ce7a4d1bf627ad7
出典データセット
uspto-grants-1976_09
特許番号
US03981905

反応ノート

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