Ammonium Chloride → HCID 17856981, compound

HRID 1784896Notes

Reaction equation

HRID 1784896 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[N+:17]([O-])=O)=[N:6][CH:7]=1.[Cl-].[NH4+]>C(O)C.O>[NH2:17][C:11]1[C:12]([OH:16])=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:20]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 17856978HCID 17856978, compound

Product 1

HCID 17856981HCID 17856981, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-(5-Bromo-2-pyridyl)-3-hydroxy-2-nitrobenzamide (7.71 g) was suspended in 50 ml of ethanol and 22 ml of distilled water, then 12.7 g of reduced iron and 2.45 g of ammonium chloride were added thereto and the mixture was heated to reflux for 6 hours. After it was cooled down to room temperature, insoluble matter was filtered and washed with chloroform. The filtrate was concentrated in vacuo, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, the mixture was extracted with chloroform and the extract was washed with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo to give 0.42 g of 2-amino-N-(5-bromo-2-pyridyl)-3-hydroxybenzamide. Then N,N-dimethylformamide was added to the insoluble matter obtained by filtration of the reaction solution, the mixture was filtered and the filtrate was concentrated in vacuo. Water was added to the resulting residue and the resulting precipitate was collected by filtration and dried in vacuo to give additional 3.28 g of the above compound. Although this contained impurities therein, it was not purified but used for the next reaction as it was.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 hours
  3. filtrationinsoluble matter was filtered
  4. washwashed with chloroform
  5. concentrationThe filtrate was concentrated in vacuo
  6. additiona saturated aqueous solution of sodium hydrogen carbonate was added
  7. extractionthe mixture was extracted with chloroform
  8. washthe extract was washed with a saturated saline solution
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9af9e730d78f44cdbede39e3d67e7fb3
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

Loading…