HCID 15278603, compound → HCID 135749814, compound

HRID 258259Notes

Reaction equation

HRID 258259 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19](N)[CH:20]=2)[CH:15]=[N:14]1.N([O-])=[O:24].[Na+]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=2)[CH:15]=[N:14]1

Participants

5

Reactant 2

HCID 15278603HCID 15278603, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135749814HCID 135749814, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

To a suspension of 1-(2,6-dichloro-4-trifluoromethylphenyl)-6-aminoindazole [Compound No. 47] (10 g) in 50% sulfuric acid (30 g), a solution of sodium nitrite (3 g) in water (10 g) was added dropwise while cooling with ice, and the resultant mixture was stirred. After 1 hour, the mixture was added dropwise for 1 hour to 10% sulfuric acid heated at 100° C. to 110° C., and the resultant mixture was refluxed for 30 minutes. After completion of the reaction, the reaction mixture was cooled and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with hexaneethyl acetate (4:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-6-hydroxyindazole (6 g).

Workup

  1. temperaturewhile cooling with ice
  2. temperatureheated at 100° C. to 110° C.
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography with hexaneethyl acetate (4:1)

Sources & evidence

ORD record
ord-6862c637633f459d976f9ed8c567ada2
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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