Hydrazine → HCID 178439404, compound

HRID 491391Notes

Reaction equation

HRID 491391 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH2:9][NH2:10]>C(O)C>[CH:2]([C:3]1[CH:4]=[C:5]([NH2:6])[NH:10][N:9]=1)([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 178439404HCID 178439404, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-methyl-3-oxopentanenitrile (0.9 g, 0.008 mole) in ethyl alcohol (5 mL) was added hydrazine (0.25 mL, 0.008 mole). The reaction mixture was refluxed for 1 hour and then cooled to room temperature. The reaction mixture was concentrated and the residue was dissolved in MeOH (2 mL). The crude product was loaded on a sulfuric acid bound resin (AG 50W-X2, hydrogen form, 100-200 mesh, BioRad), washed with MeOH (50 mL), then washed with 2N NH3 in methanol (10 mL). The ammonia washes were combined and concentrated to afford the desired product (700 mg, 68%). 1HNMR (400 MHz, MeOD) δ 5.44 (s, 1H), 2.84-2.90 (m, 1H), 1.24 (d, J=6.4 Hz).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in MeOH (2 mL)
  4. washwashed with MeOH (50 mL)
  5. washwashed with 2N NH3 in methanol (10 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70b0815cd3624d04a70d26e7f6366f92
Source dataset
uspto-grants-2009_05
Patent number
US07531539B2

Reaction notes

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