Sulfuric Acid → HCID 58980619, compound

HRID 735786Notes

Reaction equation

HRID 735786 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+].S(=O)(=O)(O)[OH:18]>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:18])=[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 aqueous sulfuric acid (9.0 M in water, 6.0 mL) and heated to 120° C. for 8 h. The solution was cooled to room temperature and NaOH (˜2.0 g) was added slowly to neutralize the solution. The mixture was then diluted with an equal volume of saturated aqueous KH2PO4 and extracted several times with 25% 2-propanol in chloroform. The extracts were combined, dried over sodium sulfate, filtered, and concentrated in vacuo 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 room temperature
  2. extractionextracted several times with 25% 2-propanol in chloroform
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3cb9919ea4841ae8a0a2f9a6c753f7b
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

Loading…