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4-Vinylpyridine → 3-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine

HRID 2230968
Notes
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Reaction equation

HRID 2230968 reaction equation
I[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:18]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[CH2:19].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:15]([C:14]1[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2](/[CH:19]=[CH:18]/[C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 75024-VinylpyridineHCID 516892Sodium Bicarbonate2×HCID 227244832-(3-Iodophenylamino)-3-nitropyridine

Product 1

HCID 227240493-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridineYield 39.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalyst
HCID 167845palladium(II) acetateCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(3-iodophenylamino)-3-nitropyridine (3.86 g), 4-vinylpyridine (1.78 g), palladium(II) acetate (80 mg), tetrabutylammonium chloride (3.14 g) and sodium bicarbonate (2.4 g) in N,N-dimethylformamide (20 ml) was stirred at 110° C. for 22 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (chloroform-methanol (50:1)) to give 3-nitro-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine (1.41 g) as an orange solid.

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-06c006dc4ee54cf887e1f6ee50d1cd48
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06426345B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes