Sodium Hydroxide → (5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazol-4-yl)acetic acid

HRID 1269873Notes

Reaction equation

HRID 1269873 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[C:7]([CH2:21][C:22]([O:24]CC)=[O:23])=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[N:10]=[CH:9]2)([O-:5])=[O:4]>O1CCOCC1>[N+:3]([C:6]1[C:7]([CH2:21][C:22]([OH:24])=[O:23])=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[N:10]=[CH:9]2)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593613ethyl (5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazol-4-yl)acetate

Product 1

HCID 69433392(5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazol-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1N-aqueous sodium hydroxide solution (8.64 ml, 8.64 mmol) was added to a solution of ethyl (5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazol-4-yl)acetate (1.92 g, 5.76 mmol) in dioxane (20 ml), and the resulting mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and water, ethyl acetate and 1N-hydrochloric acid were added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby (5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazol-4-yl)acetic acid was obtained. N,N-dimethyl-formamide (20 ml) and then potassium carbonate (800 mg, 5.79 mmol) were added thereto, and the resulting mixture was stirred at 50° C. for 30 minutes. Water, ethyl acetate, toluene and 1N-hydrochloric acid were added thereto, followed by extraction with ethyl acetate/toluene=1/1, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 4-methyl-5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole (1.39 g, 93%) was obtained.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and water, ethyl acetate and 1N-hydrochloric acid
  2. additionwere added to the residue
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-67274e60bd3842a39ef0cc4e247aafea
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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