Acetic Anhydride → 2-(4-Fluorophenyl)-1-(2-acetamido-4-pyridyl)ethanone

HRID 852314Notes

Reaction equation

HRID 852314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 110752111-(2-aminopyridin-4-yl)-2-(4-fluorophenyl)ethanone

Product 1

HCID 114826562-(4-Fluorophenyl)-1-(2-acetamido-4-pyridyl)ethanone

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

12.0 g of the compound (28) are suspended in 100 ml of acetic anhydride, a spatula tip of 4-dimethylaminopyridine is added and the reaction mixture is heated under reflux for 5 h. Most of the excess acetic anhydride is distilled off, the residue is hydrolyzed and the mixture is adjusted to pH 7 using conc. ammonia. The resulting clear precipitate (29) is filtered off and dried under reduced pressure over P2O5.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. distillationMost of the excess acetic anhydride is distilled off
  4. filtrationThe resulting clear precipitate (29) is filtered off
  5. dry with materialdried under reduced pressure over P2O5

Sources & evidence

ORD record
ord-8bbbe9b09367426a951be6f1bab21655
Source dataset
uspto-grants-2007_08
Patent number
US07253191B2

Reaction notes

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