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

HRID 978252

Reaction equation

HRID 978252 reaction equation
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

Participants

4

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 10328Indoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4044e122f59843a2bb3d40d402c12296
Source dataset
uspto-grants-1987_05
Patent number
US04663453

Linked notes

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