Isonicotinic Acid → HCID 86651051, compound

HRID 2190824Notes

Reaction equation

HRID 2190824 reaction equation
CCN=C=NCCCN(C)C.[C:12]([OH:20])(=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[NH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:37])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:24][C:23]=1[OH:38]>N1C=CC=CC=1>[OH:38][C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:37])([C:29]([F:30])([F:31])[F:32])[C:33]([F:34])([F:35])[F:36])=[CH:27][C:22]=1[NH:21][C:12](=[O:20])[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 866510652-Amino-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenol

Product 1

HCID 86651051HCID 86651051, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.58 g of WSC and 5 ml of pyridine, 0.37 g of isonicotinic acid was added. The reaction mixture was stirred at room temperature for 25 minutes. To the reaction mixture, 0.75 g of 2-amino-4-(heptafluoroisopropyl)phenol was added and was stirred while heating at 60° C. for three hours. The mixture was cooled to room temperature, and then concentrated under reduced pressure. Then, water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.79 g of N-[2-hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide.

Workup

  1. additionwas added
  2. stirringwas stirred
  3. temperaturewhile heating at 60° C. for three hours
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionThen, water was added to the residue
  7. extractionfollowed by extraction with ethyl acetate twice
  8. washThe combined organic layers were washed with water
  9. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05249ec928f842db9e20f5331129462a
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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