Hydrochloric Acid → 3-Amino-6-bromopicolinic acid

HRID 69888

Reaction equation

HRID 69888 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1.CO>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 45480453Methyl 3-amino-6-bromopyridine-2-carboxylate

Product 1

HCID 454804523-Amino-6-bromopicolinic acidYield 97%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3-amino-6-bromopicolinate (2.31 g, 10 mmoles) in 2:1 THF/MeOH (51 mL) was added 1.0 M LiOH (17 mL, 17 mmoles). After stirring for 16 hours, 1 N HCl (17 mL, 17 mmoles) was added and the THF/MeOH was removed in vacuo. The resulting solid was filtered, rinsed with cold H2O (4×20 mL) and pumped on yielding 3-amino-6-bromopicolinic acid (97%). LCMS (m/z): 216.9 (MH+); LC Rt=1.93 min.

Workup

  1. customthe THF/MeOH was removed in vacuo
  2. filtrationThe resulting solid was filtered
  3. washrinsed with cold H2O (4×20 mL)

Sources & evidence

ORD record
ord-d0e2ccb450fe471bbb99ddb873041bc0
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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