2,5-Dichloronitrobenzene → 1-(4-Chloro-2-nitrophenyl)indoline

HRID 4055

反応式

HRID 4055 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>CN(C)C=O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

参加物

4

反応物 2

HCID 69772,5-DichloronitrobenzeneHCID 10328Indoline

生成物 1

HCID 138233221-(4-Chloro-2-nitrophenyl)indoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 38.4 g (0.20 mole) of 1,4-dichloro-2-nitrobenzene and 59.6 g (0.50 mole) of indoline in 400 ml of dimethylformamide (DMF) was heated under nitrogen at 140°-145° C. overnight (23 hours). The DMF solvent was then removed in vacuo and the residue was dissolved in 500 ml of dichloromethane. This solution was extracted with H2O, with dilute hydrochloric acid, with brine, then dried over Na2SO4 and concentrated to an oil. This was adsorbed on a tall chromatography column containing 1.5 kg of silica gel packed in toluene. Elution with toluene brought forth 22.1 g (40% overall yield) of product, which crystallized. A small portion was recrystallized from hexane to afford 1-(4-chloro-2-nitrophenyl)indoline, m.p. 97°-99° C.

後処理

  1. customThe DMF solvent was then removed in vacuo
  2. dissolutionthe residue was dissolved in 500 ml of dichloromethane
  3. extractionThis solution was extracted with H2O, with dilute hydrochloric acid, with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. additioncontaining 1.5 kg of silica gel
  7. washElution with toluene
  8. custom22.1 g (40% overall yield) of product, which
  9. customcrystallized
  10. customA small portion was recrystallized from hexane

出典と根拠

ORDレコード
ord-a070677bb7a34268aa9e3cb9e14d0546
出典データセット
uspto-grants-1988_02
特許番号
US04723003

関連ノート

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