Hydrogen Bromide → 5-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

HRID 82905Notes

Reaction equation

HRID 82905 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8]O)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[BrH:11]>>[BrH:10].[NH2:1][C:2]1[C:7]([CH2:8][Br:11])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridine

Product 1

HCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Procedure

A solution of 2-amino-5-bromo-3-(hydroxymethyl)pyridine (34.6 g, 170.0 mmol) in hydrobromic acid (48% in H2O, 93 mL) was stirred at reflux overnight. The reaction mixture was cooled to room temperature, the precipitated product filtered and washed with H2O (100 mL) and dried. The title product was obtained as a light yellow solid (36.1 g, 56%, py 96.5%).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitated product filtered
  3. washwashed with H2O (100 mL)
  4. customdried

Sources & evidence

ORD record
ord-1f4bf78fbfeb472f995a5c70ab8f8c53
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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