Chlorosuccinimide → 2-Amino-5-chloro-3-nitrobenzamide

HRID 1673144Notes

Reaction equation

HRID 1673144 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:14]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 107974762-Amino-3-nitrobenzamide

Product 1

HCID 251933202-Amino-5-chloro-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-3-nitrobenzamide (4.0 g, 22 mmol) in warm acetonitrile (1250 mL) was added N-chlorosuccinimide (3.1 g, 23 mmol) and the mixture stirred at 60° C. for 20 hours. After cooling, the orange crystalline material was collected by filtration, washed with acetonitrile and dried. The filtrate was concentrated and the solid recrystallized from acetonitrile to provide a second crop of the title compound. (3.98 g, 84%). MS (DCI/NH3) m/z 216 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe orange crystalline material was collected by filtration
  3. washwashed with acetonitrile
  4. customdried
  5. concentrationThe filtrate was concentrated
  6. customthe solid recrystallized from acetonitrile

Sources & evidence

ORD record
ord-ff27052c77394258b36c8ed118e32bbe
Source dataset
uspto-grants-2011_08
Patent number
US07999117B2

Reaction notes

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