Phosphorus pentachloride → 1-Acetyl-3-[1-chloro-1-(p-tolyl)-methylidene)-5-nitro-2-indolinone

HRID 1637957Notes

Reaction equation

HRID 1637957 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:16](O)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:5]1=[O:25])(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:27]>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([Cl:27])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:5]1=[O:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178473962HCID 178473962, compound

Product 1

HCID 539550541-Acetyl-3-[1-chloro-1-(p-tolyl)-methylidene)-5-nitro-2-indolinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.55 g (10.5 mmol) of 1-acetyl-3-[1-hydroxy-1-(4-methyl-phenyl)methylidene}-5-nitro-2-indolinone and 2.40 g (11.5 mmol) of PCl5 are heated in 60 ml toluene for 2 hours at 80° C. The mixture is evaporated down in vacuo, fresh toluene is added to the evaporation residue, it is evaporated down again and this procedure is repeated once more. The evaporation residue is dissolved in a little toluene with heating. During slow cooling an isomer, probably the (Z) isomer, crystallised out. A mixture of the (Z) and (E) isomers was also obtained from the mother liquor by column chromatography on silica gel with CH2Cl2.

Workup

  1. customThe mixture is evaporated down in vacuo, fresh toluene
  2. additionis added to the evaporation residue, it
  3. customis evaporated down again
  4. dissolutionThe evaporation residue is dissolved in a little toluene
  5. temperaturewith heating
  6. temperatureDuring slow cooling an isomer
  7. customprobably the (Z) isomer, crystallised out
  8. additionA mixture of the (Z) and (E) isomers
  9. customwas also obtained from the mother liquor by column chromatography on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-6564f60d7d034d10ad137747f194177d
Source dataset
uspto-grants-2000_03
Patent number
US06043254

Reaction notes

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