Sulfuric Acid → 3-Nitropyridin-2-ylamine

HRID 636544

Reaction equation

HRID 636544 reaction equation
ClC1C=CC=C[N:3]=1.S(=O)(=O)(O)O.Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])(=O)C.[NH4+]>COCCOCCOC>[NH2:3][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 79772-ChloropyridineHCID 796132-Chloro-3-nitropyridineHCID 517165Ammonium Acetate

Product 1

HCID 778873-Nitropyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A general synthesis route begins with 2-chloropyridine which is nitrated in the presence of sulfuric acid to make 2-chloro-3-nitropyridine. This material is reacted with ammonium acetate in the presence of diglyme at about 160° C. to form 2-amino-3-nitropyridine which is reduced to form 2,3-diaminopyridine. The 2,3-diaminopyridine is reacted with 2-thiophenecarboxylic acid in the presence of polyphosphoric acid at about 125° C. to prepare 2-(2-thienyl)imidazolo [4,5]pyridine.

Workup

  1. customA general synthesis route

Sources & evidence

ORD record
ord-a5d0e9606d7b42a998db3f5e949b214e
Source dataset
uspto-grants-2001_02
Patent number
US06194430B1

Linked notes

Loading…