Potassium Carbonate → 2-Methyl-3-nitropyridine

HRID 751623Notes

Reaction equation

HRID 751623 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 574072Trimethylboroxine

Product 1

HCID 3293602-Methyl-3-nitropyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (1.00 g, 6.30 mmol), potassium carbonate (2.62 g, 18.90 mmol), tetrakis(triphenylphosphine)palladium (0.73 g, 0.63 mmol) and trimethyl boroxine (0.88 mL, 6.30 mmol) in 1,4-dioxane (2 mL) and water (8 mL) was heated to 110° C. (oil bath temperature) for 6 h and then stirred for 16 h at rt. The mixture was then filtered through a celite pad, washing through with THF. The filtrate was adsorbed onto silica gel in vacuo and purified via flash column chromatography eluting with ethyl acetate/hexanes (3:7) to give the title compound as a yellow solid. δH (CDCl3): 2.86 (3H, s), 7.34 (1H, dd), 8.26 (1H, dd), 8.71 (1H, dd).

Workup

  1. filtrationThe mixture was then filtered through a celite pad
  2. washwashing through with THF
  3. custompurified via flash column chromatography
  4. washeluting with ethyl acetate/hexanes (3:7)

Sources & evidence

ORD record
ord-f53dc7ebeecb4a15b395a781b41ad46e
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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