N-bromobutanimide → Ethyl 3-amino-6-bromopicolinate

HRID 2219584Notes

Reaction equation

HRID 2219584 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([Br:13])[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 565054Ethyl 3-aminopyridine-2-carboxylate

Product 1

HCID 25137688Ethyl 3-amino-6-bromopicolinateYield 37.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.00 g (12.04 mmol) 3-Amino-pyridine-2-carboxylic acid ethyl ester and 2.57 g (14.44 mmol, 1.2 equiv.) of N-Bromosuccinimide in 80 ml of acetonitrile was stirred for 2 h at room temperature. Silicagel (5 g) was added to the reaction mixture Which was evaporated to dryness. The residue was loaded onto a Flash chromatography column (SiO2, 50 g) and eluted with heptane/ethyl acetate 3:1. One obtains 1.11 g (4.51 mmol, 37%) of the title compound as a white cristalline solid, MS (ISP): m/e=245.1, 247.1 (M+H+).

Workup

  1. additionSilicagel (5 g) was added to the reaction mixture Which
  2. customwas evaporated to dryness
  3. washeluted with heptane/ethyl acetate 3:1

Sources & evidence

ORD record
ord-c3326a4310934d069dd74cdb03c4face
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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