Toluene → Isopropyl 5-chloro-6-isopropoxynicotinate

HRID 2189761Notes

Reaction equation

HRID 2189761 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 iodideHCID 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 (3.00 g, 17.28 mmol) was suspended in toluene (75 ml) and treated with silver carbonate (12.4 g, 24.8 mmol) and 2-iodopropane (6.9 ml, 69.12 mmol) and stirred at RT in the dark for 18 hours. The mixture was filtered and the filtrate evaporated to give the title compound with impurities (1.32 g). δH (d6-DMSO) 1.31 (6H, d), 1.35 (6H, d), 5.13 (1H, sept), 5.40 (1H, sept), 8.22 (1H, d), 8.65 (1H, d).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ab62e5603f434180abf228ddf1eecbd2
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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