Water → HCID 59355284, compound

HRID 887705Notes

Reaction equation

HRID 887705 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([CH3:11])[C:5]=1[NH2:12].[OH-].[Na+].O.C(OCC)C>CO>[NH2:12][C:5]1[C:6]([CH3:11])=[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 59355376HCID 59355376, compound

Product 1

HCID 59355284HCID 59355284, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-6-chloro-2-methylisonicotinic acid methyl ester (100 mg) was dissolved in methanol (2 mL) and 2N aqueous sodium hydroxide solution (2 mL) was added. The reaction mixture was stirred under reflux for 2.5 hours. After cooling to room temperature, water and diethyl ether were added, the layers were separated and the aqueous layer was washed with diethyl ether. The aqueous layer was acidified by addition of 2N hydrochloric acid and the formed precipitate was 3× extracted with MTB-ether. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 89 mg of the title compound of the formula

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customthe layers were separated
  3. washthe aqueous layer was washed with diethyl ether
  4. additionThe aqueous layer was acidified by addition of 2N hydrochloric acid
  5. extractionextracted with MTB-ether
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-21af994aa5f84965b0687296c9aceda4
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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