Hydrochloric Acid → (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid

HRID 546738Notes

Reaction equation

HRID 546738 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9](/[CH:11]=[CH:12]/[C:13]([O:15]CC)=[O:14])[CH:8]=[CH:7][C:6]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1.Cl>CO.C1COCC1>[CH3:3][O:4][C:5]1[N:10]=[C:9](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:8]=[CH:7][C:6]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66839136ethyl (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylate

Product 1

HCID 66633906(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acidYield 55.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 5 N sodium hydroxide solution (4 mL) was added to a solution of ethyl (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylate (1.5 g) in methanol (10 mL) and THF (6 mL). The reaction solution was stirred at room temperature for two hours, and then 5 N hydrochloric acid (5 mL) was added to the reaction solution. The generated precipitate was filtered and washed with THF to obtain 755 mg of the title compound. The property values of the compound are as follows.

Workup

  1. filtrationThe generated precipitate was filtered
  2. washwashed with THF

Sources & evidence

ORD record
ord-6d1716a32fec4f30b10013f2bc2b1451
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…