Hydrochloric Acid → HCID 13730707, compound

HRID 1650100Notes

Reaction equation

HRID 1650100 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1)[CH3:2].[OH-].[Na+].Cl>CO.O>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13730705HCID 13730705, compound

Product 1

HCID 13730707HCID 13730707, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution containing 2.5 g of methyl 5-diethylaminopicolinate in 40 ml methanol is added 40 ml water and 1.04 g of a 50% solution of NaOH in water. The mixture is heated to reflux and allowed to cool to room temperature. This is repeated. The base is neutralized with concentrated HCl, and the solvents removed in vacuo. The residue is dried azeotropically with dioxane. The residue is then extracted into ethanol. Concentration of the ethanol gives 5-diethylaminopicolinic acid as a white crystalline solid, mp 145.5°-147.5° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customthe solvents removed in vacuo
  4. dry with materialThe residue is dried azeotropically with dioxane
  5. extractionThe residue is then extracted into ethanol

Sources & evidence

ORD record
ord-9b605abce7d64f9db7c67db82198557d
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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