Hydrochloric Acid → HCID 178427868, compound

HRID 1656339Notes

Reaction equation

HRID 1656339 reaction equation
[F:1][C:2]([C:5]1[C:6](=[O:19])[C:7](N)=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]=1[CH3:11])([F:4])[F:3].Cl.N([O-])=[O:22].[Na+]>O>[F:1][C:2]([C:5]1[C:6](=[O:19])[C:7]([OH:22])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]=1[CH3:11])([F:4])[F:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 86747304HCID 86747304, compound

Product 1

HCID 178427868HCID 178427868, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 1-m.trifluoromethylphenyl-1,4-dihydro-3-amino-4-oxo-6-methylpyridazine (21 grams, 0.078 mole) in 400 ml of water is chilled. After the addition of 12N hydrochloric acid (14.5 ml), sodium nitrite (5.38 g) is added, drop by drop, with 50ml of water. After agitation of the mixture for one hour at 0° C., two hours at 20° C., and then ten minutes at 50° C., it is rechilled, filtered through sintered glass, and washed with water. The precipitate is dissolved in 1200 ml of tepid ethyl acetate. After drying over sodium sulfate, filtration and evaporation under vacuum, the product crystallizes after being dissolved in diethyl ether. There is obtained, after recrystallization from a 75/25 mixture of dioxane and diethyl ether, the Compound 1 (18.75 grams; yield=90%).

Workup

  1. additionis added
  2. customtwo hours
  3. customat 20° C.
  4. customten minutes
  5. customat 50° C.
  6. filtrationfiltered through sintered glass
  7. washwashed with water
  8. dissolutionThe precipitate is dissolved in 1200 ml of tepid ethyl acetate
  9. dry with materialAfter drying over sodium sulfate, filtration and evaporation under vacuum
  10. customthe product crystallizes
  11. dissolutionafter being dissolved in diethyl ether
  12. customThere is obtained
  13. customafter recrystallization
  14. additionfrom a 75/25 mixture of dioxane and diethyl ether

Sources & evidence

ORD record
ord-d902dfcb4caa4851a6bc646a4130634e
Source dataset
uspto-grants-1993_10
Patent number
US05254554

Reaction notes

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