Hydrochloric Acid → 3-Amino-2,6-dichloroisonicotinic acid

HRID 887699Notes

Reaction equation

HRID 887699 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([Cl:11])[C:5]=1[NH2:12].O.[OH-].[K+].Cl>C(O)C>[NH2:12][C:5]1[C:6]([Cl:11])=[N:7][C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([OH:13])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 2763082Methyl 3-Amino-2,6-dichloroisonicotinate

Product 1

HCID 593555213-Amino-2,6-dichloroisonicotinic acidYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-2,6-dichloroisonicotinic acid methyl ester (460 mg) was dissolved in ethanol (8 mL), water (2 mL) and potassium hydroxide (234 mg) was added. The solution was stirred for 20 minutes at room temperature and for 1.5 hours under reflux. After cooling to room temperature, 2N hydrochloric acid was added to adjust the pH-value to −3 and the so-formed yellow precipitate was extracted 3× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 420 mg of the title compound of the formula

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling to room temperature
  3. extractionthe so-formed yellow precipitate was extracted 3× with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-8b113a74deb3432d8538980adf6c4956
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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