1,1,2,2-Tetrachloroethane → HCID 12909448, compound

HRID 1106262Notes

Reaction equation

HRID 1106262 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[CH:14][NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10](=O)[N:9]2[CH3:23])=[CH:4][CH:3]=1.ClC(Cl)C(Cl)Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH:14]=[N:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:10]=3[N:9]2[CH3:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65911,1,2,2-TetrachloroethaneHCID 178481536HCID 178481536, compound

Product 1

HCID 12909448HCID 12909448, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The mixture of 650 mg of 1-(p-chlorophenyl)-2-methyl-4-anilinomethylidene-pyrazolidin-3,5-dione, 2.0 g of ethyl polyphosphate and 10 ml of 1,1,2,2-tetrachloroethane is refluxed for 24 hours. The solution is poured onto 10 ml of 2 N aqueous sodium hydroxide and the organic layer chromatographed on silica gel plates, using toluene:ethanol:conc. ammonium hydroxide (80:20:1) as eluent, to yield the 2-(p-chlorophenyl)-1-methyl-pyrazolo[4,3-c] quinolin-3-one with an Rf=0.48. When using dichloromethane:methanol (19:1) as eluent, said compound has the Rf=0.33; it is identical with that of Example 4.

Workup

  1. temperatureis refluxed for 24 hours
  2. customthe organic layer chromatographed on silica gel plates

Sources & evidence

ORD record
ord-9e5e558d75994a2fb807fe8bdb39510f
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

Loading…