Hydrochloric Acid → 3-Pyridinecarboxylic acid, (4-(3-(4-chlorophenyl)propoxy)phenyl)methyl ester

HRID 637475Notes

Reaction equation

HRID 637475 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1>C1C=CC=CC=1.O>[C:28]([O:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][CH:16]=1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 20256998HCID 20256998, compound

Product 1

HCID 30681633-Pyridinecarboxylic acid, (4-(3-(4-chlorophenyl)propoxy)phenyl)methyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 2.0 g (0.007 mole) of 4-[3-(4-chlorophenyl)propoxy)-phenylmethanol and 4.0 g triethylamine is added to 3.6 g (0.02 mole) of hydrochloride of nicotinoyl chloride in 50 ml of anhydrous benzene with stirring and the mixture is refluxed for 4 hrs. After cooling, water is added to the reaction mixture. The product is extracted with benzene and the extract is washed with water and dried over sodiun sulfate. Benzene is removed, the residual solid is recrystallized from ethanol to give a title compound in yield of 1.8 g (67.3%).

Workup

  1. temperaturethe mixture is refluxed for 4 hrs
  2. temperatureAfter cooling
  3. extractionThe product is extracted with benzene
  4. washthe extract is washed with water
  5. dry with materialdried over sodiun sulfate
  6. customBenzene is removed
  7. customthe residual solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-d330be54f5c34c50bd88d15c216931c0
Source dataset
uspto-grants-1985_12
Patent number
US04556715

Reaction notes

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