Hydrochloric Acid → 6-Ethoxypyridine-3-carboxylic acid

HRID 341531Notes

Reaction equation

HRID 341531 reaction equation
[OH-].[K+].[CH3:3][CH2:4][OH:5].Cl[C:7]1[N:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1.Cl>CS(C)=O>[CH2:4]([O:5][C:7]1[N:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1)[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 792226-Chloronicotinic acid

Product 1

HCID 64858176-Ethoxypyridine-3-carboxylic acidYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium hydroxide powder (0.373 g, 12.005 mmol) and EtOH (0.3 mL, 6.002 mmol) were added to a solution of 6-chloropyridine-3-carboxylic acid (0.473 g, 3.001 mmol) in DMSO (12 mL) at room temperature. The reaction mixture was heated at 100 C for 21 h, and cooled to room temperature. A 1M aqueous solution of HCl was added. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to afford the title compound (356 mg, 71%). Method B HPLC-MS: MH+ requires m/z=168. Found: m/z=168, Rt=1.50 min (95%).

Workup

  1. temperatureThe reaction mixture was heated at 100 C for 21 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-35697e9c2fa842bda444411ceeb57692
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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