Hydrochloric Acid → 2-Methoxy-6-phenylisonicotinic acid

HRID 1096963Notes

Reaction equation

HRID 1096963 reaction equation
[CH3:1][O-:2].[Na+].CO.CO.Cl[C:9]1[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=1.Cl>CC(N(C)C)=O>[CH3:1][O:2][C:9]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23694274Sodium methanolate methanol3×HCID 53485792Methyl 2-chloro-6-phenylpyridine-4-carboxylate

Product 1

HCID 579309932-Methoxy-6-phenylisonicotinic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

25% NaOMe/methanol solution (92 μL) was added to an MeOH (2 mL) solution of methyl 2-chloro-6-phenylpyridine-4-carboxylate (1100 mg), and stirred at room temperature for 2 hours. Further, 25% NaOMe/methanol solution (92 μL) was added to it, and stirred under heat with refluxing for 2 hours and 30 minutes. DMA (3 mL) was added to it, and stirred overnight at 130° C., then 25% NaOMe/methanol solution (92 μL) was added to it, and stirred at 130° C. for 7 hours. With cooling with ice, diluted hydrochloric acid was added to it, the formed precipitate was taken out through filtration, washed with water, dried, and purified through reversed-phase high-performance liquid chromatography [acetonitrile/water+0.11% trifluoroacetic acid] to obtain the title compound as a white powder.

Workup

  1. stirringstirred
  2. temperatureunder heat
  3. temperaturewith refluxing for 2 hours and 30 minutes
  4. stirringstirred overnight at 130° C.
  5. stirringstirred at 130° C. for 7 hours
  6. additionwas added to it
  7. filtrationthe formed precipitate was taken out through filtration
  8. washwashed with water
  9. customdried
  10. custompurified through reversed-phase high-performance liquid chromatography [acetonitrile/water+0.11% trifluoroacetic acid]

Sources & evidence

ORD record
ord-4398e4723afc4473b76a9bb5edd5e87a
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…