Water → 2-Pyridinecarboxylic acid, 3-[2-(3-chlorophenyl)ethyl]-

HRID 569212Notes

Reaction equation

HRID 569212 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[C:11]([C:16](NC(C)(C)C)=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:24].O.[OH-].[Na+]>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[C:11]([C:16]([OH:17])=[O:24])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 141286953-(2-(3-Chlorophenyl)ethyl)-N-(1,1-dimethylethyl)-2-pyridinecarboxamide

Product 1

HCID 112540162-Pyridinecarboxylic acid, 3-[2-(3-chlorophenyl)ethyl]-

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

3-[2-(3-chlorophenyl)ethyl]-N-(1,1-dimethylethyl)-2-pyridine carboxamide (1.0 mole, 317g), sulfuric acid (325 mL) and water (300 mL) are refluxed at about 130° C. for aporoximately 2 hours. Completeness of the reaction is determined by thin layer chromatography. The reaction mixture is cooled to about 35° C. and added to ice (2 kg). The mixture is then brought to about pH 11 with 50% sodium hydroxide. Additional ice (1 kg) is added, followed by ethyl acetate (1 liter) and hexane (525 mL). The mixture is acidified to about pH 4 with sulfuric acid and stirred for about 1 hour. Crude product is isolated by filtration, washed with water and hexane and optionally dried at about 50° C. Then the crude product is dissolved in ethyl acetate by refluxing at about 75° C. After treating the solution with decolorizing carbon (5 g), the filtrate is concentrated and cooled to about 15° C. Purified product is isolated by filtration, washed with hexane: ethyl acetate (3:1) and dried at about 50° C. A second crop may be obtained by concentrating the mother liquor and recrystallizing from ethyl acetate as described above. The yield of product is shown to be 60%.

Workup

  1. customCrude product is isolated by filtration
  2. washwashed with water and hexane
  3. customoptionally dried at about 50° C
  4. dissolutionThen the crude product is dissolved in ethyl acetate
  5. temperatureby refluxing at about 75° C
  6. additionAfter treating the solution with decolorizing carbon (5 g)
  7. concentrationthe filtrate is concentrated
  8. temperaturecooled to about 15° C
  9. customPurified product is isolated by filtration
  10. washwashed with hexane: ethyl acetate (3:1)
  11. customdried at about 50° C
  12. customA second crop may be obtained
  13. concentrationby concentrating the mother liquor
  14. customrecrystallizing from ethyl acetate

Sources & evidence

ORD record
ord-221906cc73db4807b36807a70515dfd5
Source dataset
uspto-grants-1988_03
Patent number
US04731447

Reaction notes

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