Toluene → Isopropyl 5-chloro-6-isopropoxynicotinate

HRID 2189762Notes

Reaction equation

HRID 2189762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[N:6][C:7]=1[OH:8].I[CH:13]([CH3:15])[CH3:14].[C:16]1(C)[CH:21]=CC=C[CH:17]=1>C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH:16]([CH3:21])[CH3:17])=[O:10])[CH:5]=[N:6][C:7]=1[O:8][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6362Isopropyl iodide2×HCID 178524771HCID 178524771, compound

Product 1

HCID 22985641Isopropyl 5-chloro-6-isopropoxynicotinate

Reagents, catalysts & solvents 1

HCID 178418647HCID 178418647, compoundCatalyst

Procedure

5-Chloro-6-hydroxy-3-pyridinecarboxylic acid (1 g, 5.76 mmol) was suspended in toluene (200 ml) and treated with silver carbonate (3.97 g, 14.40 mmol) and 2-iodopropane (3.46 ml, 34.6 mmol) and stirred at RT in the dark for 3 days. Added further 2-iodopropane (3 ml) and stirred for 24 hours. Added EtOAc (200 ml) and washed with water (200 ml) and saturated NaHCO3 (50 ml) followed by water (200 ml). Dried over MgSO4 and evaporated off the solvent to yield 1.0 g of the title compound as a clear, colourless oil used without further characterisation.

Workup

  1. stirringstirred for 24 hours
  2. washAdded EtOAc (200 ml) and washed with water (200 ml) and saturated NaHCO3 (50 ml)
  3. dry with materialDried over MgSO4
  4. customevaporated off the solvent

Sources & evidence

ORD record
ord-78f41beab7c3494ab952f1362d983a60
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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