Water → HCID 135749813, compound

HRID 258253Notes

Reaction equation

HRID 258253 reaction equation
C(=O)([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][C:15]=2[Cl:25])=[CH:7][C:6]=1[N+:26]([O-:28])=[O:27])OC.O>C(O)C.S(=O)(=O)(O)O>[Cl:25][C:15]1[CH:16]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:18]=[C:19]([Cl:20])[C:14]=1[N:11]1[C:12]2[C:8](=[CH:7][C:6]([N+:26]([O-:28])=[O:27])=[C:5]([OH:4])[CH:13]=2)[CH:9]=[N:10]1

Participants

5

Reactant 2

HCID 962WaterHCID 19737190HCID 19737190, compound

Product 1

HCID 135749813HCID 135749813, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of methyl 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-nitroindazol-6-yl carbonate (8 g) in ethanol (100 g), 30% sulfuric acid (20 ml) was added, and the resultant mixture was refluxed for 6 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with diethyl ether. 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-(2,6-dichloro-4-trifluoromethylphenyl)-6-hydroxy-5-nitroindazole (4.1 g).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with diethyl ether
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4fc6b11298ff494a90fb3b6e57e6153b
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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