Potassium Carbonate → 2-Methyl-3-nitropyridine

HRID 1932283Notes

Reaction equation

HRID 1932283 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11]B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 139377Methylboronic Acid

Product 1

HCID 3293602-Methyl-3-nitropyridineYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (20 g, 0.126 mol), methylboronic acid (8.3 g, 0.139 mol), tetrakis(triphenylphosphine)palladium (0) (14.58 g, 0.013 mol) and potassium carbonate (52.3 g, 0.378 mol) in anhydrous 1,4-dioxane (100 ml) was refluxed for 2 days. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 14 g of the titled compound as brown oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-5e063897c4364cf882a86bdc1d2be7c6
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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