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

HRID 1690285Notes

Reaction equation

HRID 1690285 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-f3a7da1966ed475a957f8efbc08215e5
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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