Isonicotinic Acid → HCID 52920130, compound

HRID 2094346Notes

Reaction equation

HRID 2094346 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12](O)(=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[OH-].[Na+]>>[CH2:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:1][C:2]=2[CH:7]=1)[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 5922Isonicotinic AcidHCID 14798Sodium HydroxideHCID 72113855296-63-4

Product 1

HCID 52920130HCID 52920130, compoundYield 38.1%

Conditions

Temperature
190 °C

Procedure

A mixture of 1.2 g of 2-amino-4-propylphenol, 0.98 g of isonicotinic acid and 32.8 g of polyphosphoric acid was stirred while heating at 190° C. for five hours. The mixture was cooled to room temperature and then poured into an ice-cooled aqueous solution of sodium hydroxide, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. Activated carbon was added thereto, which was filtered through Celite™. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.72 g of 5-propyl-2-(pyridin-4-yl)-benzoxazole (hereinafter, referred to as “active compound 1”).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate three times
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  5. additionActivated carbon was added
  6. filtrationwhich was filtered through Celite™
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-241eaadf3f264a5dbce2d2fc722d3afc
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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