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

HRID 12632Notes

Reaction equation

HRID 12632 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-nitrobenzamideYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-3-nitrobenzamide (4.0 g) in warm anhydrous acetonitrile (1.25 L) was treated with N-chlorosuccinimide (3.1 g) at 60° C. under nitrogen for 20 hours. The mixture was allowed to cool to room temperature and filtered. The filter cake was washed with acetonitrile and dried to provide the title compound (3.98 g, 84%). MS (DCI/NH3) m/z 216 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-caab6c8690124ab0a60e8c9035a4719f
Source dataset
uspto-grants-2010_06
Patent number
US07728026B2

Reaction notes

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