HCID 178516568, compound → HCID 178515186, compound

HRID 1106260Notes

Reaction equation

HRID 1106260 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[CH:14]O)[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)=[N:9]2)=[CH:4][CH:3]=1>O1CCCC1.[Pt]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][NH:22][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178516568HCID 178516568, compound

Product 1

HCID 178515186HCID 178515186, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The solution of 308 mg of 1-(p-chlorophenyl)-4-hydroxymethylene-3-(o-nitrophenyl)-4,5-dihydropyrazol-5-one in 80 ml of tetrahydrofuran is hydrogenated over 50 mg of 5% platinum on charcoal at room temperature and 3 atmospheres for 0.5 hour. The mixture is filtered, the filtrate evaporated and the residue taken up in 150 ml of toluene. To the solution, 0.1 ml of conc. hydrochloric acid is added, and the mixture refluxed at a water separator for 18 hours. It is cooled, the precipitate formed filtered off and purified by preparative thin layer chromotography, using ethyl acetate:ethanol:conc. ammonium hydroxide (17:3:3) as developing solvent on silica gel, to yield the 2-(p-chlorophenyl)-pyrazolo[4, 3-c]quinolin-3(5H)-one melting at 327°, it is identical with that of Example 1.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated
  3. additionTo the solution, 0.1 ml of conc. hydrochloric acid is added
  4. temperaturethe mixture refluxed at a water separator for 18 hours
  5. temperatureIt is cooled
  6. customthe precipitate formed
  7. filtrationfiltered off
  8. custompurified by preparative thin layer chromotography

Sources & evidence

ORD record
ord-cec6d39fc0c242d8b946ee0ab62a23d4
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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