Ammonium Hydroxide → 6-Bromo-4-nitropyridine-2-carboxamide

HRID 1603628Notes

Reaction equation

HRID 1603628 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[NH4+:14].[OH-]>CN(C)C=O.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:14])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 221765006-Bromo-4-nitropicolinic acid

Product 1

HCID 196055336-Bromo-4-nitropyridine-2-carboxamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.3 g (0.00526 mol) of 6-bromo-4-nitropyridine-2-carboxylic acid were dissolved in 10 ml of dimethylformamide, treated at 5° C. with 0.94 g (0.0058 mol) of 1,1-carbonyldiimidazole and subsequently stirred at room temperature for 3 hrs. Then, 40 ml of 25% NH4OH in water was added thereto and the mixture was stirred at room temperature for 1 hr. The reaction mixture was partitioned in water and dichloromethane and the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There were obtained 1.1 g (85%) of 6-bromo-4-nitropyridine-2-carboxamide as white crystals; m.p.: 179-180° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customThe reaction mixture was partitioned in water
  3. washdichloromethane and the organic phase was washed with water and sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-212ac70086824335903e90948a08ea31
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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