Hydrochloric Acid → HCID 12886960, compound

HRID 441850Notes

Reaction equation

HRID 441850 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14](N)=[CH:13][CH:12]=2)=[CH:9][N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:7]=1)=[O:5])[CH3:2].Cl.N([O-])=O.[Na+].[OH-].[Na+].S(OC)([O:34][CH3:35])(=O)=O>[Cl-].[Zn+2].[Cl-].O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:34][CH3:35])=[CH:13][CH:12]=2)=[CH:9][N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 12886956HCID 12886956, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12886960HCID 12886960, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent2×

Procedure

2.4 gm. of 4-(4-aminophenyl)-1-phenyl-3-pyrazolecarboxylic acid ethyl ester are reacted with 28 ml. of 1N hydrochloric acid, cooled to 0° C. and slowly diazotized with a solution of 830 mg. of sodium nitrite in 10 ml. of water. The mixture is diluted with 10 ml. of water and stirred for 15 minutes at 0° C. Thereupon, 953 mg. of zinc chloride are added to the mixture, which is allowed to stand for 30 minutes. The separated precipitate is filtered under vacuum, dried and taken up in 50 ml. of methanol and allowed to stand at room temperature for 16 hours, and then is heated for one hour under reflux. The reaction mixture is concentrated under vacuum and the residue is dissolved in benzene. The benzene phase is washed and concentrated in vacuum. The residue is reacted with 2 equivalents of sodium hydroxide and 2.02 g. of dimethyl sulfate and heated at 80° C. for 30 minutes. After cooling, the mixture is extracted with methylene chloride, the organic phase is concentrated and the residue is recrystallized from isopropanol. 1.92 g. of 4-(4-methoxyphenyl)-1-phenyl-3-pyrazolecarboxylic acid ethyl ester with a melting point of 94° C., is obtained.

Workup

  1. additionThe mixture is diluted with 10 ml
  2. filtrationThe separated precipitate is filtered under vacuum
  3. customdried
  4. waitto stand at room temperature for 16 hours
  5. temperatureis heated for one hour
  6. temperatureunder reflux
  7. concentrationThe reaction mixture is concentrated under vacuum
  8. dissolutionthe residue is dissolved in benzene
  9. washThe benzene phase is washed
  10. concentrationconcentrated in vacuum
  11. temperatureAfter cooling
  12. extractionthe mixture is extracted with methylene chloride
  13. concentrationthe organic phase is concentrated
  14. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-dbdfee6d2198405ba752ddab21dcdf71
Source dataset
uspto-grants-1977_08
Patent number
US04042706

Reaction notes

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