Hydrochloric Acid → 2-(1H-Pyrrol-1-yl)isonicotinic acid

HRID 1673363Notes

Reaction equation

HRID 1673363 reaction equation
[OH-].[Na+].CO.[N:5]1([C:10]2[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6]1.Cl>C(OCC)(=O)C.O1CCCC1>[N:5]1([C:10]2[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=[CH:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18945326HCID 18945326, compound

Product 1

HCID 336950532-(1H-Pyrrol-1-yl)isonicotinic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 mL of 2.0 mol/L aqueous sodium hydroxide was added to a mixed solution of 4.0 mL of methanol and 4.0 mL of tetrahydrofuran containing 0.47 g of methyl 2-(1H-pyrrol-1-yl)pyridine-4-carboxylate and stirred at room temperature for 1 hour. 5.0 mL of 1.0 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture sequentially. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated, under reduced pressure. Diisopropyl ether was added to the obtained residue and a solid substance was removed by filtration to obtain 0.39 g of 2-(1H-pyrrol-1-yl)pyridine-4-carboxylic acid as white solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. washafter washed with a saturated sodium chloride aqueous solution
  4. customthe solvent was evaporated, under reduced pressure
  5. additionDiisopropyl ether was added to the obtained residue
  6. customa solid substance was removed by filtration

Sources & evidence

ORD record
ord-fcf0c91503ae400ead762584a02cf8a8
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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