O-Xylene → HCID 178515186, compound

HRID 1106244Notes

Reaction equation

HRID 1106244 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1.C1(C)C(C)=CC=CC=1.[OH-].[Na+]>O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:12](=[O:14])[C:3]3=[CH:4][NH:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]3=[N:25]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 70624(4-Chlorophenyl)hydrazineHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

Product 1

HCID 178515186HCID 178515186, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 1,681 g of ethyl 4-chloro-quinoline-3-carboxylate, 1,017 g of p-chlorophenylhydrazine and 25 L of xylene is heated to 105° for 24 hours while stirring under nitrogen. The resulting suspension is cooled to 20°, combined with 14 L of 2 N aqueous sodium hydroxide, stirred for 15 minutes and diluted with 30 L of water. Stirring is continued for 1 hour, the aqueous phase separated, washed five times with 8 L of diethyl ether each, filtered and the filtrate treated with the solution of 1,600 g of ammonium chloride in 8 L of water while stirring under nitrogen. The resulting suspension is stirred overnight at room temperature, filtered and the residue washed 5 times with 12 L of hot water. This residue is dried at 5 mmHg and 90° and 1,665 g thereof are dissolved in 8.4 L of dimethylformamide at 130°. The solution is filtered and allowed to cool to room temperature while stirring. The resulting suspension is filtered, washed twice with 500 ml of cold dimethylformamide each, four times with 1 L of diethyl ether and the residue is dried at 0.1 mmHg and 100°, to yield the 2-(p-chlorophenyl)-pyrazolo[4,3-c]quinolin-3(5H)-one of the formula ##STR9## melting at 324°-327° with decomposition.

Workup

  1. temperatureis heated to 105° for 24 hours
  2. temperatureThe resulting suspension is cooled to 20°
  3. stirringstirred for 15 minutes
  4. stirringStirring
  5. customthe aqueous phase separated
  6. washwashed five times with 8 L of diethyl ether each,
  7. filtrationfiltered
  8. additionthe filtrate treated with the solution of 1,600 g of ammonium chloride in 8 L of water
  9. stirringwhile stirring under nitrogen
  10. stirringThe resulting suspension is stirred overnight at room temperature
  11. filtrationfiltered
  12. washthe residue washed 5 times with 12 L of hot water
  13. customThis residue is dried at 5 mmHg and 90° and 1,665 g
  14. dissolutionthereof are dissolved in 8.4 L of dimethylformamide at 130°
  15. filtrationThe solution is filtered
  16. stirringwhile stirring
  17. filtrationThe resulting suspension is filtered
  18. washwashed twice with 500 ml of cold dimethylformamide each, four times with 1 L of diethyl ether
  19. customthe residue is dried at 0.1 mmHg and 100°

Sources & evidence

ORD record
ord-4ce109ca7ddd49dfbeb45e62ec53f407
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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