2-Chloro-3-nitropyridine → 3-Nitro-2-vinylpyridine

HRID 1784877Notes

Reaction equation

HRID 1784877 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([Sn](CCC)(CCC)C=C)[CH2:12]C>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.C1(C)C=CC=CC=1>[N+:8]([C:7]1[C:2]([CH:11]=[CH2:12])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 21909134Tripropyl-vinyl-stannane

Product 1

HCID 118296173-Nitro-2-vinylpyridineYield 54%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 0.92 g (5.80 mmol) of 2-chloro-3-nitro-pyridine, 1.60 g (5.80 mmol) tripropyl-vinyl-stannane, 0.335 g (0.290 mmol) Pd(PPh3)4 and 10 mL of toluene were combined and refluxed under an inert atmosphere overnight. After routine aqueous workup the crude product was purified by chromatography on silica gel to give 0.470 g (54% yield) of 3-nitro-2-vinyl-pyridine.

Workup

  1. temperaturerefluxed under an inert atmosphere overnight
  2. customAfter routine aqueous workup the crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4582bbaa9e704aacbe4a92fcf7710903
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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