Acetic Anhydride → Acetamide, N,N-(2,2'-dipyridyl)-

HRID 1471249Notes

Reaction equation

HRID 1471249 reaction equation
[CH:1]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[N:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:7]([C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=1)[C:14](=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 145472,2'-Dipyridylamine

Product 1

HCID 52053Acetamide, N,N-(2,2'-dipyridyl)-

Procedure

To a flask were added 2,2′-dipyridylamine and 12 ml acetic anhydride. The mixture was heated to 110 C under nitrogen for 5 hours and cooled to 22 C. After quenching with a slow addition of aqueous sodium bicarbonate, the mixture was made basic with the addition of small portions of sodium carbonate. The product was extracted with ethyl acetate and after removal of solvent, it was purified by silica gel chromatography using 65% ethyl acetate in hexane to give 0.8 g of an oil.

Workup

  1. temperatureThe mixture was heated to 110 C under nitrogen for 5 hours
  2. temperaturecooled to 22 C
  3. customAfter quenching with a slow addition of aqueous sodium bicarbonate
  4. additionthe mixture was made basic with the addition of small portions of sodium carbonate
  5. extractionThe product was extracted with ethyl acetate
  6. customafter removal of solvent, it
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-dd53d894e65943d394d658ab7a8ef5ec
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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