Water → 3-AMINO-2-BROMO-6-CHLOROISONICOTINIC ACID

HRID 887706Notes

Reaction equation

HRID 887706 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([Br:11])[C:5]=1[NH2:12].[OH-].[Na+].C(OCC)C.O>CO>[NH2:12][C:5]1[C:6]([Br:11])=[N:7][C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([OH:13])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 59355453Methyl 3-amino-2-bromo-6-chloro-4-pyridinecarboxylate

Product 1

HCID 593553373-AMINO-2-BROMO-6-CHLOROISONICOTINIC ACID

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (260 mg) (example 3, step 5) was dissolved in methanol (2 mL), 2N aqueous sodium hydroxide solution (2 mL) was added and the reaction mixture was stirred for 2 hours at reflux. After cooling to room temperature, diethyl ether and water were added and the layers were separated. The aqueous layer was washed with diethyl ether and acidified by addition of 2N hydrochloric acid. The formed precipitate was extracted with MTB-ether (3×), the combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 246 mg of

Workup

  1. temperatureat reflux
  2. customthe layers were separated
  3. washThe aqueous layer was washed with diethyl ether
  4. additionacidified by addition of 2N hydrochloric acid
  5. extractionThe formed precipitate was extracted with MTB-ether (3×)
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuum
  9. customto afford 246 mg of

Sources & evidence

ORD record
ord-eba12bab327142c098fcb7e4972ccede
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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