Sulfuric Acid → HCID 58980619, compound

HRID 1787456Notes

Reaction equation

HRID 1787456 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]#N)([CH3:4])([CH3:3])[CH3:2].[OH-:15].[Na+].[OH:17]S(O)(=O)=O>OP([O-])(O)=O.[K+]>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]([OH:17])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58980642HCID 58980642, compound

Product 1

HCID 58980619HCID 58980619, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 516951Monobasic potassium phosphateSolvent

Conditions

Temperature
120 °C

Procedure

The above nitrile (1.10 g, 5.68 mmol) was dissolved in H2SO4 (9.0 M, 6.0 mL) and heated to 120° C. for 8 h. The solution was cooled to rt and NaOH (˜2.0 g) was added slowly to neutralize the solution. The mixture was then diluted with an equal volume of saturate KH2PO4 and extracted several times with 25% 2-propanol in chloroform. The extracts were combined, dried over Na2SO4, filtered, and concentrated to provide 2-tert-butyl-5-methoxy-isonicotinic acid (1.09 g, 92%) as a pale brown solid which was utilized without further purification.

Workup

  1. temperatureThe solution was cooled to rt
  2. extractionextracted several times with 25% 2-propanol in chloroform
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2098bb350c534b2f9829123494dd1978
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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