Isopropyl iodide → 6-Chloro-3-nitro-2-(propan-2-yloxy)pyridine

HRID 518831Notes

Reaction equation

HRID 518831 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.I[CH:13]([CH3:15])[CH3:14]>C(=O)([O-])[O-].[Ag+2].CCCCCCC>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:13]([CH3:15])[CH3:14])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 178526634HCID 178526634, compound

Product 1

HCID 108464126-Chloro-3-nitro-2-(propan-2-yloxy)pyridineYield 88.5%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
130 °C

Procedure

1.63 g of 6-chloro-3-nitropyridin-2-ol, 66 ml of heptane, 3.175 g of 2-iodopropane and 3.09 g of silver carbonate are introduced. The reaction medium is microwave-heated at 130° C. for 10 minutes and is then evaporated to dryness, bound to silica and purified by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of heptane and ethyl acetate (90/10). 1.79 g of 6-chloro-3-nitro-2-(propan-2-yloxy)pyridine are obtained in the form of a beige solid.

Workup

  1. customis then evaporated to dryness
  2. custompurified by flash chromatography on silica gel (40-63 μm), elution
  3. additionbeing carried out with a mixture of heptane and ethyl acetate (90/10)

Sources & evidence

ORD record
ord-0a2ef25f34474426ab1740565d69ad0d
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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