Acetic Anhydride → N-(2,6-Dichloro-3-nitropyridin-4-yl)acetamide

HRID 876846Notes

Reaction equation

HRID 876846 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([Cl:12])[N:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:13](=[O:15])[CH3:14])[CH:5]=[C:4]([Cl:12])[N:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 2827402,6-Dichloro-3-nitropyridin-4-amine

Product 1

HCID 86671443N-(2,6-Dichloro-3-nitropyridin-4-yl)acetamide

Procedure

2,6-Dichloro-3-nitropyridin-4-amine (208 mg, 1 mmol) was added to acetic anhydride (2 mL), and the reaction mixture was refluxed overnight. After cooled to room temperature, the reaction mixture was basified with aqueous Na2CO3 until the pH was 8. The resulting mixture was then extracted with CH2Cl2. The organic layer was separated, dried over Na2SO4, and concentrated to afford the title compound (240 mg), which was used for the next step without further purification. MS (m/z): 250 (M+1)+.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. extractionThe resulting mixture was then extracted with CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec893d57474544bda06dc18930bb1ba4
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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