Water → HCID 12673422, compound

HRID 127358Notes

Reaction equation

HRID 127358 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([O:17][CH2:18]Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].O>CC(C)=O.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:18][O:17][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 762582-Chloronicotinic acidHCID 87885Chloromethyl pivalate

Product 1

HCID 12673422HCID 12673422, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

Into a suspension of 2-chloro-3-pyridinecarboxylic acid (23.7 g) in 500 ml of acetone, triethylamine (30.7 ml) is added. After 30 minutes of stirring, pivaloyloxymethyl chloride (22.5 ml) is poured into the reaction mixture, and the resulting mixture heated to reflux for 2 hours. The mixture is then cooled to a temperature of 15°-20° C., and then poured into 1000 ml of cooled water. The resulting mixture is then extracted with methylene chloride (2×100 ml), and the water layer discarded. To the remaining organic extract, 10 g of anhydrous magnesium sulfate is added and then separated by filtration. The organic extract is distilled at normal pressures to separate methylene chloride. When all methylene chloride is distilled off, the distillation is continued under vacuum (0.17 mm Hg) to separate the desired product compound. The distilled product fraction separates at 131°-133° C., and is pivaloyloxymethyl 2-chloro-3-pyridine-carboxylate. Yield: 21.8 g (53.5% of theory).

Workup

  1. additionis added
  2. temperaturethe resulting mixture heated
  3. temperatureto reflux for 2 hours
  4. temperatureThe mixture is then cooled to a temperature of 15°-20° C.
  5. extractionThe resulting mixture is then extracted with methylene chloride (2×100 ml)
  6. additionTo the remaining organic extract, 10 g of anhydrous magnesium sulfate is added
  7. customseparated by filtration
  8. extractionThe organic extract
  9. distillationis distilled at normal pressures
  10. customto separate methylene chloride
  11. distillationWhen all methylene chloride is distilled off
  12. distillationthe distillation
  13. customto separate the desired product compound
  14. customseparates at 131°-133° C.

Sources & evidence

ORD record
ord-03c4f3e431a04ff8ad9a7e8174101a0e
Source dataset
uspto-grants-1981_03
Patent number
US04255581

Reaction notes

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