Water → 4-Amino-3-nitropyridine

HRID 1583646Notes

Reaction equation

HRID 1583646 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].O.[OH-].[NH4+]>C(N(CC)CC)C.C(OCC)(=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

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 124074974-Ethoxy-3-nitropyridine hydrochloride

Product 1

HCID 5488034-Amino-3-nitropyridineYield 86.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

A 500 ml 3-neck round bottom flask equipped with a condenser, thermometer and mechanical stirrer was charged with 78.4 g (0.383 mol) of 4-ethoxy-3-nitropyridine hydrochloride, 118.1 g (1.53 mol) of ammonium acetate and 183 ml of water. The stirred reaction mixture was refluxed for 71/2 hours and the progress of the reaction was followed by thin layer chromatography employing a 10:1 ethyl acetate:triethylamine solvent system. The reaction flask was chilled to approximately 4° C. after the pH of the mixture was adjusted from 5.2 to 8.1 with 60 ml of concentrated ammonium hydroxide. The yellow precipitate was collected by filtration, washed twice with chilled water and dried under vacuum at 50° C. for 10 hours. A total dry weight of 46.15 g (86.6% yield) of 3-nitro-4-aminopyridine was obtained. The product was verified by NMR and compared to an authentic sample.

Workup

  1. customA 500 ml 3-neck round bottom flask equipped with a condenser
  2. customThe stirred reaction mixture
  3. temperaturewas refluxed for 71/2 hours
  4. filtrationThe yellow precipitate was collected by filtration
  5. washwashed twice with chilled water
  6. customdried under vacuum at 50° C. for 10 hours

Sources & evidence

ORD record
ord-cbec9c5c3fe84ccb85245d9cf5f63416
Source dataset
uspto-grants-1985_11
Patent number
US04552967

Reaction notes

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