Hydrochloric Acid → Ethyl 6-chloropicolinate

HRID 706721Notes

Reaction equation

HRID 706721 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:12][CH2:13]O>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:12][CH3:13])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 208126-Chloropicolinic acid

Product 1

HCID 11063114Ethyl 6-chloropicolinateYield 85%

Procedure

To 6-chloropicolinic acid (5.01 g, 31.8 mmol) in EtOH (100 mL) was added concentrated HCl (6 mL, 78 mmol). The reaction was heated to reflux for overnight, cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and NaOH (2M) aqueous solution was added until pH=8. The aqueous layer was then extracted with DCM. The combined organic extracts were combined, dried (Na2SO4) and concentrated under reduced pressure to give the desired product (85%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for overnight
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (100 mL)
  5. additionNaOH (2M) aqueous solution was added until pH=8
  6. extractionThe aqueous layer was then extracted with DCM
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-336a65bc60514981b4cbbb45292c4bf7
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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