Ammonium Acetate → 4-Amino-3-nitropyridine

HRID 1583649Notes

Reaction equation

HRID 1583649 reaction equation
Cl.C(O[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])C.C([O-])(=O)C.[NH4+:18]>C(O)C>[N+:11]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[NH2:18])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 124074974-Ethoxy-3-nitropyridine hydrochloride

Product 1

HCID 5488034-Amino-3-nitropyridineYield 118.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

A 50 ml 3-neck round bottom flask fitted with a condenser, thermometer and mechanical stirrer was charged with 3.0 g (14.66 mmol) of 4-ethoxy-3-nitropyridine hydrochloride, 6.1 g (79.9 mmol) of ammonium acetate and 6.7 ml of absolute ethanol. The reaction mixture was refluxed for approximately 24 hours and cooled to about 4° C. The pH of the solution was adjusted to 8.0 with base and the precipitated solid was collected by filtration. The product was rinsed with chilled ethanol and dried in vacuo at 50° C. to afford 2.41 g of 3-nitro-4-aminopyridine (and a small amount of ammonium acetate). The identity of the product was verified by NMR comparison to an authentic sample.

Workup

  1. customA 50 ml 3-neck round bottom flask fitted with a condenser
  2. temperatureThe reaction mixture was refluxed for approximately 24 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe product was rinsed with chilled ethanol
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-088bf9c9ee7643c3b25b2ae8cb5fea28
Source dataset
uspto-grants-1985_11
Patent number
US04552967

Reaction notes

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