2-Chloro-3-nitropyridine → 2-Mesityl-3-nitropyridine

HRID 966013Notes

Reaction equation

HRID 966013 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]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.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>[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[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 796132-Chloro-3-nitropyridineHCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acid

Product 1

HCID 222494912-Mesityl-3-nitropyridineYield 78.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 107951,1-DimethoxyethaneSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (5.0 g, 31.5 mmol), mesitylboric acid (5.65 g, 34.7 mmol), Pd(PPh3)4 (1.82 g, 1.58 mmol) and barium hydroxide octahydrate (14.9 g, 47.3 mmol) in 2,2-dimethoxyethane (150 mL) and water (25 mL) was heated under reflux for one day. The mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (5.99 g) as pale yellow oil.

Workup

  1. temperatureunder reflux for one day
  2. filtrationThe mixture was filtered through Celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a57792c7b9cd41bbaae7d13ab09d2eb3
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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