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

HRID 1926502Notes

Reaction equation

HRID 1926502 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-fd68458bca0d472f9d8fe159708341a5
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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