Methylhydrazine → HCID 86724103, compound

HRID 1748761Notes

Reaction equation

HRID 1748761 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH2:9][C:10]#[N:11])[CH:5]=[CH:4][CH:3]=1.[CH3:13][NH:14][NH2:15]>C(O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[N:14]([CH3:13])[N:15]=[C:10]([NH2:11])[CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 534172293-(6-Bromopyridin-2-yl)-3-oxopropanenitrile

Product 1

HCID 86724103HCID 86724103, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(6-bromo-2-pyridyl)-3-oxo-propanenitrile (1.71 g, 7.6 mmol, Preparation A.1) in ethanol (50 mL) was added methyl hydrazine (1.20 mL, 22.8 mmol). The resulting mixture was stirred for about 30 min at rt and then heated under reflux for about 4 h. After cooling to rt the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:2) to give 3-(6-bromo-2-pyridyl)-2-methyl-pyrazol-5-amine (1.56 g, 6.2 mmol, 81%) as an off white solid: 1H-NMR (CDCl3, Bruker 400 MHz) δ 3.57 (2 H, br s); 3.75 (3 H, s); 5.90 (1 H, s); 7.34 (1 H, d, J=8 Hz); 7.52 (1 H, t, J=8 Hz); 7.82 (1 H, d, J=8 Hz).

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 4 h
  3. temperatureAfter cooling to rt the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by column chromatography (SiO2, ethyl acetate/hexanes 1:2)

Sources & evidence

ORD record
ord-0cb92ebb57f04cf6a45ae4546b535f65
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

Loading…