Sulfuric Acid → HCID 178498115, compound

HRID 416571Notes

Reaction equation

HRID 416571 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[C:16]1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 11430Potassium CarbonateHCID 178418543HCID 178418543, compound

Product 1

HCID 178498115HCID 178498115, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-hydroxynicotinic acid (3-067-01) (50 g) in methanol (500 ml) were added conc. sulfuric acid (15 ml) and toluene (100 mL) at room temperature. After the reaction mixture was stirred for 28 h attached Dienstark reflux tube and neutralized with an aqueous potassium carbonate solution, the solvent was evaporated. To the residue were added aqueous saturated ammonium chloride solution and chloroform, and the organic layer was separated, and the aqueous layer was extracted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 2-hydroxynicotinic acid methyl ester (3-067-02) (46 g, 84%) as a white solid.

Workup

  1. temperaturereflux tube
  2. customthe solvent was evaporated
  3. additionTo the residue were added aqueous saturated ammonium chloride solution and chloroform
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dc4e39f386264f54b331d1bb4335e178
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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