Hydrochloric Acid → 6-(Pyrrolidin-1-ylmethyl)picolinic acid

HRID 876552Notes

Reaction equation

HRID 876552 reaction equation
[N:1]1([CH2:6][C:7]2[N:12]=[C:11]([C:13]([O:15]C)=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C.O>[N:1]1([CH2:6][C:7]2[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15123266HCID 15123266, compound

Product 1

HCID 463182346-(Pyrrolidin-1-ylmethyl)picolinic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of methyl 6-(pyrrolidin-1-ylmethyl)picolinate 73 (36 g) and NaOH (40 g, 1.0 mol) in ethanol/H2O (320 mL) was stirred at 75° C. for 16 h. The pH was adjusted to 7 with 3N HCl and extracted with EtOAc. The aqueous layer was concentrated to dryness and extracted with dichloromethane/methanol (v:v=3:1), The organic layer was dried to give 74 (27 g, 55% yield).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe aqueous layer was concentrated to dryness
  3. extractionextracted with dichloromethane/methanol (v:v=3:1)
  4. customThe organic layer was dried

Sources & evidence

ORD record
ord-90727b22a5634900b5310f687a8e0f31
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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