Acetic Anhydride → HCID 5303010, compound

HRID 1741014Notes

Reaction equation

HRID 1741014 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[N:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.C(OC(=O)C)(=O)C>>[N:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:6]/[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 5303010HCID 5303010, compoundYield 99.1%

Procedure

To 15.1 g of 2-nitrobenzaldehvde was added 9.3 g of 4-picoline followed by addition of 5 ml of acetic anhydride and the mixture was refluxed for 12 hours. This reaction mixture was poured in ice-water, made basic with 2N--NaOH, and extracted with chloroform. The extract was dehydrated over anhydrous magnesium sulfate and the solvent was evaporated off to provide 22.40 g of (E)-2-[2-(4-pyridyl)ethenyl]-1-nitrobenzene. This product was treated as in Reference Example 2 (2) to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. extractionNaOH, and extracted with chloroform
  3. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-f674700be2f4440e972516fc729489a2
Source dataset
uspto-grants-1999_10
Patent number
US05972976

Reaction notes

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