Methylhydrazine → ethyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

HRID 875082Notes

Reaction equation

HRID 875082 reaction equation
C([O:3][C:4]1[C:5](=O)[CH:6]([C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH:9]=1)C.[CH3:18][NH:19][NH2:20]>C(O)(=O)C>[CH3:18][N:19]1[C:5]2[C:4](=[O:3])[CH2:9][CH2:8][CH2:7][C:6]=2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:20]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 44235432Ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate

Product 1

HCID 44236352ethyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

30 g (0.125 mol) of ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate were dissolved in 150 mL of glacial acetic acid and 6.5 mL of methylhydrazine were added. The mixture was stirred at room temperature for 6 hours. The solvent was then evaporated and the crude redissolved with water, the solution made basic with 30% NH4OH and extracted with chlorform. The organic layer was then dried over Na2SO4 and concentrated. The residue was chromatographed on a silica gel column (eluant: chloroform) and crystallized from a mixture n-hexane/diethyl ether (TLC chloroform; 63% yield as a white solid).

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe crude redissolved with water
  3. extractionextracted with chlorform
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column (eluant: chloroform)
  7. customcrystallized from a mixture n-hexane/diethyl ether (TLC chloroform

Sources & evidence

ORD record
ord-a02c56b628ef4032812625535c8124b5
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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