Bromine → Methyl 6-amino-5-bromopicolinate

HRID 451449Notes

Reaction equation

HRID 451449 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[N:6]=1)=[O:4].[Br:12]Br>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:12])=[C:7]([NH2:11])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 13809143Methyl 6-aminopyridine-2-carboxylate

Product 1

HCID 10704661Methyl 6-amino-5-bromopicolinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22%).

Workup

  1. washwashed with saturated sodium thiosulfate solution and water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67f67d2110d34c09923e379d10c57fed
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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