3-Pyridinemethanol → HCID 12713103, compound

HRID 2052418Notes

Reaction equation

HRID 2052418 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1>C1C=CC=CC=1>[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:1][CH2:2][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:15])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 12713103HCID 12713103, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
20 °C

Procedure

10.5 g. of 3-hydroxymethyl-pyridine are dissolved in 60 ml. of anhydrous benzene. The solution is stirred at 20° C. and 7.6 g. of 4-fluorobenzoic acid chloride dissolved in 60 ml. of benzene are added dropwise thereto. The reaction mixture is refluxed for 30 minutes and then cooled to 20° C. The precipitated 3-hydroxymethyl-pyridine hydrochloride is filtered off. The filtrate is extracted with 250 ml. of 5% aqueous hydrochloric acid. The separated aqueous acidic layer is washed with 50 ml. of diethyl ether and then adjusted to pH=9 with 20% aqueous sodium carbonate solution. The basified solution is extracted three times with 50 ml. each of diethyl ether, the combined ether extracts are dried with anhydrous sodium sulfate, filtered and the filtrate is evaporated. The evaporation residue is dissolved in 80 ml. of a 1:1 mixture of isopropanol and ether and etheric hydrogen chloride solution is added to adjust the pH-value to 2. The precipitated acid addition salt is separated by filtration and recrystallized from a mixture of equal values of acetone and ethanol. 8.5 g. of 3-[ (4-fluorobenzoyl)-oxymethyl]-pyridine (67.7% of theoretical yield) are obtained; m.p.: 142°-143° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. temperaturecooled to 20° C
  3. filtrationThe precipitated 3-hydroxymethyl-pyridine hydrochloride is filtered off
  4. extractionThe filtrate is extracted with 250 ml
  5. washThe separated aqueous acidic layer is washed with 50 ml
  6. extractionThe basified solution is extracted three times with 50 ml
  7. dry with materialeach of diethyl ether, the combined ether extracts are dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated
  10. dissolutionThe evaporation residue is dissolved in 80 ml
  11. additionof a 1:1 mixture of isopropanol and ether and etheric hydrogen chloride solution
  12. additionis added
  13. additionThe precipitated acid addition salt
  14. customis separated by filtration
  15. customrecrystallized from a mixture of equal values of acetone and ethanol

Sources & evidence

ORD record
ord-5e9a488b05d549cf846ba047aee56a4d
Source dataset
uspto-grants-1980_01
Patent number
US04184040

Reaction notes

Loading…