Methyl iodide → HCID 89666817, compound

HRID 2171219Notes

Reaction equation

HRID 2171219 reaction equation
IC.[C:3](=O)([O-])[O-].[Cs+].[Cs+].[OH:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=2)[N:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:11]=1>CC(C)=O>[CH3:3][O:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=2)[N:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178473418HCID 178473418, compound

Product 1

HCID 89666817HCID 89666817, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

Iodomethane (10 ml) and cesium carbonate (4.89 g) were added to an acetone (20 ml) solution containing ethyl 3-hydroxy-5-nitro-1H-indazol-1-carboxylate (2.51 g) obtained in the 2nd step under ice cooling in a nitrogen atmosphere, followed by stirring at 80° C. for 0.5 hours. An insoluble precipitate was removed by filtration and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1). A white solid of ethyl 3-methoxy-5-nitro-1H-indazol-1-carboxylate (1.24 g) was thus obtained.

Workup

  1. customobtained in the 2nd step under ice cooling in a nitrogen atmosphere
  2. customAn insoluble precipitate was removed by filtration
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record
ord-4fae5d3ae55b41bb9d7f4ab87969c6f5
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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