Potassium Carbonate → Nicotinic Acid

HRID 1739461Notes

Reaction equation

HRID 1739461 reaction equation
C([O-])([O-])=O.[K+].[K+].BrC[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][N:10]=1>CN(C=O)C>[N:10]1[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=[CH:14][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 127522376-Bromomethyl-nicotinic acid methyl ester

Product 1

HCID 938Nicotinic AcidYield 298.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the 4-bromo-2-(2-phenethyl)phenol (1.25 g, 14.5 mmol in DMF (10 ml) was treated with K2CO3 (0.82 g, 5.96 mmol) and methyl 2-bromomethyl-5-pyridine carboxylate (1.14 g, 4.96 mmol). The reaction was stirred at ambient temperature and then evaporated in vacuo. The residue was partitioned between ethyl acetate/H2O and the combined organic extracts were washed with at NaCl solution, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl acetate/hexane) to give methyl 2-(2-phenethyl)-4-bromophenoxy methyl)-5-pyridinecarboxylic acid (1.82 g, 95%).

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate/H2O
  3. washthe combined organic extracts were washed with at NaCl solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (eluant: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87c19e3acc49471ab8cc24ff40025bf0
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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