2-Amino-5-bromo-3-(hydroxymethyl)pyridine hydrobromide → 5-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

HRID 1825929Notes

Reaction equation

HRID 1825929 reaction equation
[BrH:1].[NH2:2][C:3]1[C:8]([CH2:9]O)=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1>Br>[BrH:11].[NH2:2][C:3]1[C:8]([CH2:9][Br:1])=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 441196112-Amino-5-bromo-3-(hydroxymethyl)pyridine hydrobromide

Product 1

HCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromideYield 172.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A suspension of 2-amino-5-bromo-3-(hydroxymethyl)pyridine hydrobromide (289 g, 1.02 mole) in 48% aqueous HBr (2.9 L) was heated at reflux for 12 hrs. Complete solution occurred during heating. The reaction mixture was cooled and a crystalline precipitate formed. This was filtered and washed with ethyl acetate and air dried to give the title compound (305 g, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hrs
  3. temperatureduring heating
  4. temperatureThe reaction mixture was cooled
  5. customa crystalline precipitate formed
  6. filtrationThis was filtered
  7. washwashed with ethyl acetate and air
  8. customdried

Sources & evidence

ORD record
ord-8fce600c78fb4bde863c2ffc224f6da9
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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