N-bromobutanimide → 2-Amino-5-bromo-3-(hydroxymethyl)pyridine

HRID 1920982Notes

Reaction equation

HRID 1920982 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([Br:17])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-3-(hydroxymethyl)pyridine (13.0 g, 116.0 mmole) in CH2Cl2 (300 mL) at RT was added NBS (22.71 g, 127.6 mmole). After stirring at RT for 45 min the reaction solution was concentrated and the residue was dissolved in CHCl3. The resulting suspension was filtered and the filtrate was concentrated to a dark oil. Purification on silica gel (EtOAc) afforded the title compound (78%, 18.36 g) as a tan solid: MS (ES) m/e 204 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in CHCl3
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated to a dark oil
  5. customPurification on silica gel (EtOAc)

Sources & evidence

ORD record
ord-6c6404a8629c461880079970853c653c
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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