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

HRID 2112635Notes

Reaction equation

HRID 2112635 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-7751407efc86454aa39f0d4f56ef8ed7
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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