Pyridine → HCID 66880243, compound

HRID 2094491Notes

Reaction equation

HRID 2094491 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[Cl:8][C:7]1[C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][CH:4]=[C:3]([OH:13])[C:2]=1[NH:1][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66880908HCID 66880908, compound

Product 1

HCID 66880243HCID 66880243, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.17 g of 2-amino-3-chloro-4-trifluoromethylphenol, 0.99 g of isonicotinic acid, 0.19 g of WSC and 3 ml of pyridine was stirred while heating at 80° C. for two hours. The mixture was cooled to room temperature, and then water was poured, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.15 g of N-[2-chloro-6-hydroxy-3-(trifluoromethyl)phenyl]isonicotinamide.

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, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-533b3d43057843c0a348677c5c41adfd
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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