Acetic Anhydride → 5-Acetamido 2-chloronicotinonitrile

HRID 1074608Notes

Reaction equation

HRID 1074608 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11](OC(=O)C)(=[O:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>O>[C:11]([NH:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 204962095-Amino-2-chloropyridine-3-carbonitrile

Product 1

HCID 204962065-Acetamido 2-chloronicotinonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-amino-2-chloronicotinonitrile (2.6 g, 0.017 m) and acetic anhydride (50 ml) was heated at reflux for 30 minutes. After cooling to 25°, the reaction mixture was poured into water, neutralized with saturated Na2CO3 solution and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated to dryness. The residue was recrystallized from benzene/hexane to yield 2.5 g (76% yield) of 5-acetamido 2-chloronicotinonitrile.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureAfter cooling to 25°
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-c712c817824a4b47b4bf589b7fe49eaf
Source dataset
uspto-grants-1983_07
Patent number
US04393212

Reaction notes

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