Hydrochloric Acid → HCID 21291163, compound

HRID 622610Notes

Reaction equation

HRID 622610 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1C(O)=O.Cl.C(O)(C)C>O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 13755218HCID 13755218, compound

Product 1

HCID 21291163HCID 21291163, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.5 g (0.06 mole) of 5-amino-1-(3,5-dichloropyrid-2-yl)-pyrazole-4-carboxylic acid are slowly heated to 80° C. in a mixture of 150 ml of water, 75 ml of concentrated hydrochloric acid and 20 ml of isopropanol and the reaction mixture is stirred at this temperature until the evolution of gas has ended. The clear solution formed is evaporated to dryness, the residue is suspended in methylene chloride, the suspension is neutralized with aqueous sodium carbonate solution, the organic phase is separated off and the aqueous phase is extracted twice more with methylene chloride. The combined organic phases are dried over sodium sulphate and freed from the solvent in vacuo. 12.7 g (92% of theory) of 5-amino-1-(3,5-dichloropyrid-2-yl)-pyrazole are obtained as an oil. 1H-NMR (CDCl3 /TMS as the internal standard): δ=4.55; 5.55; 7.43; 7.88; and 8.30 ppm.

Workup

  1. customThe clear solution formed
  2. customis evaporated to dryness
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted twice more with methylene chloride
  5. dry with materialThe combined organic phases are dried over sodium sulphate

Sources & evidence

ORD record
ord-c102212c87f64211b4f02953b575ed7a
Source dataset
uspto-grants-1988_09
Patent number
US04772312

Reaction notes

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