Hydrochloric Acid → HCID 19086712, compound

HRID 1464572Notes

Reaction equation

HRID 1464572 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([F:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=3[Cl:25])[CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl>CO>[Cl:25][C:15]1[CH:16]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:18]=[C:19]([F:20])[C:14]=1[O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[N:5][NH:4]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54063817HCID 54063817, compound

Product 1

HCID 19086712HCID 19086712, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Acetyl-6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy) indazole (2.05 g) was stirred and heated under reflux with methanol (10 cm3) and concentrated hydrochloric acid (6 cm3) for 2 hours and then left to stand at room temperature for 48 hours. The solvent was removed under vacuum and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with water, dried (MgSO4), filtered and the solvent removed from the filtrate under vacuum. The residue, a brown oil, was purified by flash chromatography (CHCl3 :ethyl acetate-85:15) to yield 6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)indazole (1.32 g) as a straw colored oil which solidified on standing. m.p.=133.9°-143.1° C. M+ =330.

Workup

  1. temperatureheated
  2. waitleft
  3. customThe solvent was removed under vacuum
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  5. washThe organic phase was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed from the filtrate under vacuum
  9. customThe residue, a brown oil, was purified by flash chromatography (CHCl3 :ethyl acetate-85:15)

Sources & evidence

ORD record
ord-b7f40659226e4ba5a4df8d4052541ef4
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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