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

HRID 1710501Notes

Reaction equation

HRID 1710501 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-456674500b8a4873999664590353e558
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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