Acetoxyacetyl chloride → 2-(Acetoxyacetylamino)-6-nitrobenzonitrile

HRID 2248761Notes

Reaction equation

HRID 2248761 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].[C:13]([O:16][CH2:17][C:18](Cl)=[O:19])(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:16][CH2:17][C:18]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5])=[O:19])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 127157292-Amino-6-nitrobenzonitrile

Product 1

HCID 149862822-(Acetoxyacetylamino)-6-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-6-nitrobenzonitrile (6.5 g) in pyridine (100 ml) is cooled in an ice bath and thereto is added dropwise acetoxyacetyl chloride (4.4 ml). The mixture is stirred at room temperature for 1 hour, and thereafter, pyridine is distilled off under reduced pressure, and then water is added thereto, and the mixture is extracted with methylene chloride. The organic layer is washed with 1N hydrochloric acid and dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The resulting crude crystals are recrystallized from ethanol to give the title compound (5.8 g) having the following physical properties.

Workup

  1. distillationpyridine is distilled off under reduced pressure
  2. additionwater is added
  3. extractionthe mixture is extracted with methylene chloride
  4. washThe organic layer is washed with 1N hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe resulting crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-6c0f96e5dae34bae80d214d5299054b8
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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