Methylhydrazine → HCID 66579566, compound

HRID 1428331Notes

Reaction equation

HRID 1428331 reaction equation
O=[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]#[N:5].[CH3:12][NH:13][NH2:14]>C(O)C>[CH3:12][N:13]1[C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[CH:3][C:4]([NH2:5])=[N:14]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 157315343-Oxo-3-(3-pyridinyl)propanenitrile

Product 1

HCID 66579566HCID 66579566, compoundYield 6.14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (8.53 ml) was added 3-oxo-3-(pyridin-3-yl)propanenitrile (0.82 g, 5.61 mmol) and methylhydrazine (0.25 g, 5.61 mmol) and stirred at reflux for 2 hours. The reaction was cooled to room temperature and concentrated to dryness. The crude material was purified by silica gel chromatography by eluting with 0-20% MeOH/dichloromethane to yield two products—1-methyl-5-(pyridin-3-yl)-1H-pyrazol-3-amine (0.060 g; 6.14%): 1H NMR (300 MHz, CDCl3) δ 8.72 (s, 1H), 8.53 (d, 1H), 7.76-7.63 (m, 1H), 7.43-7.33 (m, 1H), 5.75 (s, 1H), 3.76-3.57 (m, 5H) and 1-methyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine (0.150 g, 15.35%): 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 8.48 (d, 1H), 7.99 (d, 1H), 7.38-7.07 (m, 1H), 585 (s, 1H), 3.80-3.59 (m, 5H).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated to dryness
  3. customThe crude material was purified by silica gel chromatography
  4. washby eluting with 0-20% MeOH/dichloromethane

Sources & evidence

ORD record
ord-14d4e1a6b2cd4b1886616edbd110c329
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

Loading…