Ammonium Chloride → 3-Amino-5-bromopyridine-2-carboxamide

HRID 2422683Notes

Reaction equation

HRID 2422683 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:11][C:4]1[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 672444665-Bromo-3-nitropyridine-2-carboxamide

Product 1

HCID 210758623-Amino-5-bromopyridine-2-carboxamideYield 70%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-Bromo-3-nitropyridine-2-carboxamide (400 mg, 1.63 mmol), ammonium chloride (435 mg, 8.15 mmol) and iron powder (273 mg, 4.89 mmol) were suspended in methanol (6 mL) and water (3 mL), and stirred at 100° C. for 20 hours. After cooled to room temperature, this was filtered through Celite, and the Celite was washed with methanol. The mother liquid was concentrated, and the residue was dissolved in chloroform and washed with water. The organic layer was concentrated under reduced pressure to obtain the intended compound (246 mg, 70%).

Workup

  1. filtrationthis was filtered through Celite
  2. washthe Celite was washed with methanol
  3. concentrationThe mother liquid was concentrated
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5cc439fcd934ff79d355efdd282b6b3
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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