Hydrazine hydrate (1:1) → HCID 178422057, compound

HRID 530024Notes

Reaction equation

HRID 530024 reaction equation
[CH3:1][CH:2]([C:5](=O)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:3]#[N:4].O.[NH2:14][NH2:15]>CCO>[CH3:1][C:2]1[C:5]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:14][NH:15][C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 431572262-methyl-3-oxo-3-(pyridin-3-yl)propanenitrile

Product 1

HCID 178422057HCID 178422057, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-3-oxo-3-(pyridin-3-yl) propanenitrile (1.5 g, 9.4 mmol) in EtOH (20 mL) was added 85% hydrazine hydrate (2 mL). The resulting mixture was heated to reflux for 2 hours. After cooling to rt, the solvent was removed in vacuo and the crude product purified by column chromatography (DCM:MeOH=10:1) to give the desired product: MS (m/z): 175.0 [M+H]+, 1HNMR (400 MHz, CD3OD) δ 8.71 (d, 1H, J=2.0 Hz), 8.50-8.51 (m, 1H), 7.99 (d, 1H, J=8.0 Hz), 7.50-7.55 (m, 1H), 2.06 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe solvent was removed in vacuo
  4. customthe crude product purified by column chromatography (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-7f20a7c0dbe048e386bcd30bb2b0aa98
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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