Toluene → Isopropyl 5-chloro-6-isopropoxynicotinate

HRID 423338Notes

Reaction equation

HRID 423338 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

The 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. LC/MS showed 2/3 product. Added 2-iodopropane (3 ml) and stirred for 24 hours. LC/MS showed 80% product. Added EtOAc (200 ml) and washed with water (200 ml)+sat. 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. MS (ES+) C12H1635ClNO3 requires 257; found 257.

Workup

  1. washAdded EtOAc (200 ml) and washed with water (200 ml)+sat
  2. dry with materialDried over MgSO4
  3. customevaporated off the solvent

Sources & evidence

ORD record
ord-fa6f43bd31f8450d93483381c8dad3df
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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