Hydrochloric Acid → HCID 19737195, compound

HRID 258250Notes

Reaction equation

HRID 258250 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][C:17](N)=[CH:18][CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.N([O-])=O.[Na+].[ClH:26]>O>[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:26])=[CH:18][CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19737196HCID 19737196, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19737195HCID 19737195, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5-aminoindazole [Compound No. 7] (3.0 g) in conc. hydrochloric acid (30 g), the solution of sodium nitrite (0.6 g) in water (1 ml) was added dropwise while cooling with ice, and the resultant mixture was stirred at room temperature. After 30 minutes, cuprous chloride (CuCl) (3 g) was added thereto, and the resultant mixture was stirred for 1 hour. After completion of the reaction, the reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5-chloroindazole (2.0 g).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-fa12608ce20d4b8883cf898ec76b5fad
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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