Hydrogen Bromide → 5-Bromo-4,6-dimethylpicolinonitrile

HRID 1043922Notes

Reaction equation

HRID 1043922 reaction equation
N[C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].[BrH:12].BrBr.N([O-])=O.[Na+].[OH-].[Na+]>>[Br:12][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 24408BromineHCID 23668193Sodium NitriteHCID 866863445-Amino-4,6-dimethylpicolinonitrile

Product 1

HCID 866863465-Bromo-4,6-dimethylpicolinonitrile

Procedure

5-amino-4,6-dimethylpicolinonitrile (390 mg) was added to aqueous hydrogen bromide (2.9 mL). Bromine (164 μl) and sodium nitrite (467 mg) were added to the solution at 0° C. The solution was warmed to room temperature and stirred for four hours. A 5 N aqueous sodium hydroxide solution was added to the reaction mixture, followed by separation with ethyl acetate. The organic layer was washed with brine and then dried using magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 30%) to give the title compound (300 mg).

Workup

  1. customfollowed by separation with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 30%)

Sources & evidence

ORD record
ord-8b2541b7abf544d29eea10d7fdb67a99
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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