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

HRID 1914728Notes

Reaction equation

HRID 1914728 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 69.1%

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 (0.125 mol) were added. The mixture was stirred at room temperature for 6 hours. The solvent was then evaporated and the crude redissolved in water, made basic with 30% NH4OH and extracted with dichlormethane. The organic layer was then dried over Na2SO4 and concentrated. The residue was crystallized from diethyl ether to give 19.2 g (68% yield) of title compound.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe crude redissolved in water
  3. extractionextracted with dichlormethane
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-e1259f4cf5d84544abf0ac11d708476a
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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