Sulfuric Acid → Ethyl 2-bromoisonicotinate

HRID 1069064

Reaction equation

HRID 1069064 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[C:11]1(C)C=CC=C[CH:12]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:11]([O:9][C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)=[O:10])[CH3:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 2227012-Bromoisonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3847769Ethyl 2-bromoisonicotinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-bromo4-pyridine carboxylic acid (prepared according to the method of Ashimori, Chem. Pharm. Bull. 38 (9) 2446-2458 (1990)) in 2:1 toluene: absolute ethanol (45 mL) was added sulfuric acid (0.75 mL). The mixture was heated at reflux for 16 h. The mixture was poured into saturated aqueous sodium bicarbonate and extracted with chloroform (3 times). The combined chloroform extracts were dried over magnesium sulfate, filtered and concentrated afforded the crude product as a yellow oil. Purification by silica gel chromatography eluting with 9:1 hexane:ethyl acetate to afford the title compound (900 mg) as a clear, colorless oil.

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 16 h
  4. extractionextracted with chloroform (3 times)
  5. dry with materialThe combined chloroform extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customafforded the crude product as a yellow oil
  9. customPurification by silica gel chromatography
  10. washeluting with 9:1 hexane

Sources & evidence

ORD record
ord-87d436ec62d7494299d612f339bfac85
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Linked notes

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