Hydrogen Bromide → 6-Bromo-4-methylpyridin-2-amine

Reaction equation

[BrH:1].O[C:3]([CH3:10])([CH2:7][C:8]#[N:9])[CH2:4][C:5]#[N:6].C(=O)([O-])O.[Na+]>>[Br:1][C:5]1[N:6]=[C:8]([NH2:9])[CH:7]=[C:3]([CH3:10])[CH:4]=1

Participants

Reactant 3

HCID 260Hydrogen Bromide

HCID 516892Sodium Bicarbonate

HCID 127207073-Hydroxy-3-methylpentanedinitrile

Product 1

HCID 221765076-Bromo-4-methylpyridin-2-amine

Procedure

Hydrogen bromide solution (33 wt. % in acetic acid) (17.8 ml, 98.92 mmol) was added dropwise to 3-hydroxy-3-methyl-pentanedinitrile (3.07 g, 24.73 mmol) with stirring. The reaction was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate was added until neutralised. The resulting white precipitate was collected by filtration, washed with water and dried under vacuum to give the desired product. Yield 2.55 g, 55%. LCMS MI: 186.89+188.91, RT: 3.16 min, Method: 2.