Ammonium Acetate → 4-Amino-3-nitropyridine
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)(=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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 22 liter 4-neck flask fitted with a reflux condenser, thermometer and mechanical stirrer was charged with 1300 g (6.35 mol) of 4-ethoxy-3-nitropyridine hydrochloride, 2438 g (31.62 mol) of ammonium acetate and 13 1. of glacial acetic acid. The reaction mixture was refluxed for 3 hours and cooled. The volatiles were evaporated under reduced pressure and the residue was dissolved in 1N hydrochloric acid. The insoluble material was removed by filtration and the pH of the filtrate was adjusted to approximately 8.5 with concentrated ammonium hydroxide. The precipitated solid was collected by filtration, washed with water and dried in a forced air oven to provide 701 g of 3-nitro-4-aminopyridine. Yield 79.3%. mp=187°-195° C. The identity of the product was also confirmed by chromatography in a 10:1 ethyl acetate:triethylamine solvent system by comparison to a reference standard.
Workup
- customA 22 liter 4-neck flask fitted with a reflux condenser
- temperatureThe reaction mixture was refluxed for 3 hours
- temperaturecooled
- customThe volatiles were evaporated under reduced pressure
- dissolutionthe residue was dissolved in 1N hydrochloric acid
- customThe insoluble material was removed by filtration
- filtrationThe precipitated solid was collected by filtration
- washwashed with water
- customdried in a forced air oven
Sources & evidence
- ORD record
- ord-97483b4383a24bbc9a7a037062f4137e
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04552967
Reaction notes
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