Pyridine → 2-Acetamido-5-nitropyridine

HRID 2263080Notes

Reaction equation

HRID 2263080 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>O1CCCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:17](=[O:19])[CH3:18])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 778882-Amino-5-nitropyridine

Product 1

HCID 3451252-Acetamido-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-nitropyridine (13.9 g, 100 mmol) and pyridine (24 ml, 300 mmol) in tetrahydrofuran (300 ml) was added dropwise acetyl chloride (10.7 ml, 150 mmol) with ice-cooling, the mixture was stirred at room temperature for 1 hour. To the mixture was added dropwise acetyl chloride (10.7 ml, 150 mmol) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice-water and the desired product (14.5 g, 80.1%) as a solid was collected by filtration.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationthe desired product (14.5 g, 80.1%) as a solid was collected by filtration

Sources & evidence

ORD record
ord-7606771efc2f4a85bdbb3e9b9ff232fe
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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