Chlorosuccinimide → HCID 17856977, compound

HRID 1784897Notes

Reaction equation

HRID 1784897 reaction equation
[NH2:1][C:2]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][N:8]=1)=[O:5].[Cl:19]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:17]([OH:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][N:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 17856981HCID 17856981, compound

Product 1

HCID 17856977HCID 17856977, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Amino-N-(5-bromo-2-pyridyl)-3-hydroxybenzamide (1.99 g) and 990 mg of N-chlorosuccinimide were dissolved in 30 ml of N,N-dimethylformamide, the solution was stirred at 50° C. for 2 hours and the insoluble matter was filtered off. The solvent was evaporated in vacuo, water was added to the resulting residue and the precipitate was collected by filtration. This was dried in vacuo, purified by means of a silica gel column chromatography, water was added to the resulting crudely purified product and the resulting precipitate was collected by filtration and dried in vacuo to give 1.12 g of 2-amino-N-(5-bromo-2-pyridyl)-5-chloro-3-hydroxybenzamide.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. customThe solvent was evaporated in vacuo, water
  3. additionwas added to the resulting residue
  4. filtrationthe precipitate was collected by filtration
  5. customThis was dried in vacuo
  6. custompurified by means of a silica gel column chromatography, water
  7. additionwas added to the resulting crudely purified product
  8. filtrationthe resulting precipitate was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-3b1ce6b5af8745e2a725956aee0de433
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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