Water → 4-Amino-3-nitropyridine

HRID 1583647Notes

Reaction equation

HRID 1583647 reaction equation
C(O[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])C.C([O-])(=O)C.[NH4+:17].C(OCC)(=O)C.O>C(N(CC)CC)C>[N+:10]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[NH2:17])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 3563054-Ethoxy-3-nitropyridineHCID 517165Ammonium Acetate

Product 1

HCID 5488034-Amino-3-nitropyridineYield 75%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

A 25 ml round bottom flask was fitted with a reflux condenser and magnetic stirrer and placed in an oil bath. The flask was charged with 1.0 g (5.95 mmol) of 4-ethoxy-3-nitropyridine and 5.0 g (65 mmol) of ammonium acetate. The reaction mixture was heated at 120° C. to provide a homogeneous liquid. The progress of the reaction was followed by thin layer chromotography employing a 10:1 ethyl acetate:triethylamine solvent system. After 21/2 hours the reaction mixture was cooled and poured into water. The yellow precipitate was collected by filtration, washed with water and dried in vacuo at 60° C. over phosphorus pentoxide. A total of 620 mg of 3-nitro-4-aminopyridine was obtained and chromatographically verified by comparison to an authentic reference standard. Yield 75%.

Workup

  1. customA 25 ml round bottom flask was fitted with a reflux condenser and magnetic stirrer
  2. customplaced in an oil bath
  3. customto provide a homogeneous liquid
  4. temperatureAfter 21/2 hours the reaction mixture was cooled
  5. filtrationThe yellow precipitate was collected by filtration
  6. washwashed with water
  7. dry with materialdried in vacuo at 60° C. over phosphorus pentoxide

Sources & evidence

ORD record
ord-782f5a81e6464ae886879de6b864f4cf
Source dataset
uspto-grants-1985_11
Patent number
US04552967

Reaction notes

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