Methylhydrazine → 2-Methyl-4,5,6,7-tetrahydro-2H-indazol-3-amine

HRID 1477753Notes

Reaction equation

HRID 1477753 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]#[N:9].[CH3:10][NH:11][NH2:12]>C(O)C>[CH3:10][N:11]1[C:8]([NH2:9])=[C:3]2[C:2]([CH2:7][CH2:6][CH2:5][CH2:4]2)=[N:12]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 2202972-Oxocyclohexanecarbonitrile

Product 1

HCID 529036082-Methyl-4,5,6,7-tetrahydro-2H-indazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-oxocyclohexanecarbonitrile 16 (10 g, 81.2 mmol) and methyl hydrazine 15 (3 equiv, 11.2 g) in 150 mL of absolute ethanol was refluxed for 20 hrs and was concentrated on rotavapor to dryness. The crude product was recrystallized from methanol to afford the desired product 17. (Reference for the preparation of compound 17: J. Am. Chem. Soc. 1959, 81, 2448-2452)

Workup

  1. concentrationwas concentrated on rotavapor to dryness
  2. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-6a5f6d51909b408ba06cc759631d3e73
Source dataset
uspto-grants-2016_08
Patent number
US09403815B2

Reaction notes

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