Nitric Acid → HCID 19737198, compound

HRID 258255Notes

Reaction equation

HRID 258255 reaction equation
[C:1](=[O:25])([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)=[CH:7][CH:6]=1)[O:2][CH3:3].[N+:26]([O-])([OH:28])=[O:27]>S(=O)(=O)(O)O>[C:1](=[O:25])([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)=[CH:7][C:6]=1[N+:26]([O-:28])=[O:27])[O:2][CH3:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19737197HCID 19737197, compound

Product 1

HCID 19737198HCID 19737198, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of methyl 1-(3-chloro-5-trifluoromethylpyridin-2-yl)indazol-6-yl carbonate [Compound No. 39] (10 g) in conc. sulfuric acid (100 g), fuming nitric acid (3.5 g) was added dropwise while cooling with ice, and the resultant mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into ice water, and the precipitated crystals were collected by filtration, washed and dried. The crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give methyl 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5-nitroindazol-6-yl carbonate (8.2 g).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter completion of the reaction
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed
  5. customdried
  6. customThe crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-6bc64312249e464c8d5c9bd34ebf1243
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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