Potassium Carbonate → 2-Methyl-3-nitropyridine

HRID 1887692Notes

Reaction equation

HRID 1887692 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+]>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.O1CCOCC1>[CH3:11][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 3293602-Methyl-3-nitropyridineYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The mixture of 2-chloro-3-nitropyridine (50 g, 0.315 mol, 1.0 eq), TMB (50 mL, 1.1 eq), (PPh3)4Pd (O) (36.4 g, 0.1 eq), K2CO3 (130.6 g, 3.0 eq) and dioxane (1500 mL) was refluxed under argon for 2 days. The mixture was cooled to room temperature and filtered through a celite pad to remove K2CO3 and catalyst. The celite pad was washed with EtOAc. The organic solutions were combined and concentrated to get the crude which was purified by silica gel chromatography (0%˜40% EtOAc/Hex) to obtain the desired product 2-methyl-3-nitropyridine (30.5 g, isolated yield 70%) (Note: isolated yield 42% was obtained when the reaction was refluxed for 24 h).

Workup

  1. temperaturewas refluxed under argon for 2 days
  2. filtrationfiltered through a celite pad
  3. customto remove K2CO3 and catalyst
  4. washThe celite pad was washed with EtOAc
  5. concentrationconcentrated
  6. customto get the crude which
  7. customwas purified by silica gel chromatography (0%˜40% EtOAc/Hex)

Sources & evidence

ORD record
ord-4dead94c08ef4248ac9b4d8a83f37836
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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