Hydrazine hydrate (1:1) → HCID 178461432, compound

HRID 1943911Notes

Reaction equation

HRID 1943911 reaction equation
[CH3:1][CH:2]1[CH2:4][CH:3]1[C:5](=O)[CH2:6][C:7]#[N:8].O.[NH2:11][NH2:12]>C(O)C>[CH3:1][C@H:2]1[CH2:4][C@H:3]1[C:5]1[CH:6]=[C:7]([NH2:8])[NH:12][N:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 431156733-(2-Methylcyclopropyl)-3-oxopropanenitrile

Product 1

HCID 178461432HCID 178461432, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-(2-Methylcyclopropyl)-3-oxopropanenitrile (0.240 g, 1.95 mmol) was dissolved in dry ethanol (3 mL). Hydrazine monohydrate (0.728 mL, 9.75 mmol) was added, and the reaction mixture was heated to 80° C. for 20 minutes. The reaction mixture was then cooled to room temperature and concentrated. Silica gel chromatography (5% MeOH/DCM) provided a mixture of cis and trans isomers which were separated by chiral HPLC providing 3-(cis-2-methylcyclopropyl)-1H-pyrazol-5-amine (74 mg, 28% for two steps) as an oil.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. customSilica gel chromatography (5% MeOH/DCM) provided
  4. additiona mixture of cis and trans isomers which
  5. customwere separated by chiral HPLC

Sources & evidence

ORD record
ord-3aab3f36f3704539ae2b4190066f0697
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…