Water → HCID 15278584, compound

HRID 258249Notes

Reaction equation

HRID 258249 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[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.O>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 197371941-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-6-nitro-1H-indazole

Product 1

HCID 15278584HCID 15278584, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of iron powder (5 g) in acetic acid (10 g), 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-6-nitroindazole [Compound No. 3] (3 g) and water (10 g) were added, and the resultant mixture was refluxed for 3 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was poured into water 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 hexane-ethyl acetate (4:1) to give 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-6-aminoindazole (1.8 g).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. additionthe filtrate was poured into water
  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 hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-fa1040216f0945768c8af71578636599
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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