Hydrochloric Acid → 4-(5-pentylpyridin-2-yl)benzoic acid

HRID 1198829Notes

Reaction equation

HRID 1198829 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][N:10]=1)#N.[OH-:20].[K+].Cl.[CH2:23]([OH:29])COCCO>>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C:4]2[CH:3]=[CH:8][C:7]([C:23]([OH:29])=[O:20])=[CH:6][CH:5]=2)=[N:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 19867194HCID 19867194, compound

Product 1

HCID 20536714-(5-pentylpyridin-2-yl)benzoic acid

Conditions

Temperature
175 °C

Procedure

A mixture of 3.026 g of 2-(cyanophenyl)-5-pentylpyridine, 125 ml of diethylene glycol and 13.8 g of potassium hydroxide was heated to 175° C. for 1.5 hours while stirring and gassing with nitrogen. The reaction mixture was then left to cool, adjusted to pH 8 with semi-concentrated hydrochloric acid and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulphate, filtered and concentrated. The crude p-(5-pentyl-2-pyridyl)benzoic acid obtained was recrystallized from acetone/hexane.

Workup

  1. waitThe reaction mixture was then left
  2. temperatureto cool
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-769311d1227f4266ad3460577a88a9e4
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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