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

HRID 1971601Notes

Reaction equation

HRID 1971601 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

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 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.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2c3fdcb908484150a810ed6e2ded73b2
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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