5-Aminonicotinic acid

Off-white Cryst

5-aminonicotinic acid is an aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring. It has a role as a metabolite. It is an aromatic amine, an aminopyridine and an aminonicotinic acid. It derives from a nicotinic acid.

To a mixture of 5-bromo-3-pyridinecarboxylic acid (i. e. the product of Step A) (25 g, 0.124 mol) in aqueous ammonia (67.32 mL) was added copper sulphate pentahydrate (8.41 g), and the reaction mixture heated in an autoclave at [120 C] for 16 h. Progress of the reaction was monitored by thin layer chromatography, using ninhydrin to visualize the product. The reaction mixture was washed with saturated solution of sodium sulfide to remove copper ions and was then acidified to a pH of about 4-5 using concentrated hydrochloric acid, causing a solid to separate as the acidified mixture cooled. The solid was collected using filtration and dried to provide the title compound (12.9 g, 74percent yield).Copper [(II)] sulfate (12.5g, [50MMOL)] was added to 5-bromo-nicotinic acid (50g, [248MMOL)] in aqueous ammonium hydroxide solution (d = 0.88). The reaction was sealed in an autoclave reactor and heated at [180°C] for 15 hours. The mixture was cooled, diluted with water [(300MUT), ] sodium sulfite [(13.] 5g, [173MMOL)] was added and the mixture stirred for 20 minutes. The black precipitate was filtered away through celite, and the filtrate was adjusted to pH 3-4 upon treatment with 2M HCI. The mixture was filtered through celite and the filtrate concentrated to [200ML] volume upon which a white precipitate formed. The solution was cooled, filtered and the solid dried under vacuum at [40°C] overnight to give the title compound (22g, 159mmol, 64percent). 'NMR [(400MHZ, ] d6-DMSO) 5.60 (2H, broad s), 7.41 (1H, d, J=3Hz), 8.10 [(1H, ] d, J=3Hz), 8.24 (1H, d, J=3Hz), 13.05 (1 H, broad s). GC/MS [MH+] 139.To a stirred solution of 5-Aminonicotinic acid (1g, .7.2mmmol) was suspended in methanol (100ml) and thionyl chloride (4.22ml, 57.9mmol) added dropwise at O0C. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was evaporated to dryness and the resultant yellow oil was re-dissolved in methanol/ether (1:1) and afforded yellow crystals (HCI salt) which were collected by filtration, yield 1.2g (85%). LCMS purity 91%, m/z 153 [M++H]+, To a mixture of 5-bromo-3-pyridinecarboxylic acid (i. e. the product of Step A) (25 g, 0.124 mol) in aqueous ammonia (67.32 mL) was added copper sulphate pentahydrate (8.41 g), and the reaction mixture heated in an autoclave at [120 C] for 16 h. Progress of the reaction was monitored by thin layer chromatography, using ninhydrin to visualize the product. The reaction mixture was washed with saturated solution of sodium sulfide to remove copper ions and was then acidified to a pH of about 4-5 using concentrated hydrochloric acid, causing a solid to separate as the acidified mixture cooled. The solid was collected using filtration and dried to provide the title compound (12.9 g, 74% yield).Copper [(II)] sulfate (12.5g, [50MMOL)] was added to 5-bromo-nicotinic acid (50g, [248MMOL)] in aqueous ammonium hydroxide solution (d = 0.88). The reaction was sealed in an autoclave reactor and heated at [180C] for 15 hours. The mixture was cooled, diluted with water [(300MUT), ] sodium sulfite [(13.] 5g, [173MMOL)] was added and the mixture stirred for 20 minutes. The black precipitate was filtered away through celite, and the filtrate was adjusted to pH 3-4 upon treatment with 2M HCI. The mixture was filtered through celite and the filtrate concentrated to [200ML] volume upon which a white precipitate formed. The solution was cooled, filtered and the solid dried under vacuum at [40C] overnight to give the title compound (22g, 159mmol, 64%). 'NMR [(400MHZ, ] d6-DMSO) 5.60 (2H, broad s), 7.41 (1H, d, J=3Hz), 8.10 [(1H, ] d, J=3Hz), 8.24 (1H, d, J=3Hz), 13.05 (1 H, broad s). GC/MS [MH+] 139.

Molecular Weight:138.12
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:138.042927438
Monoisotopic Mass:138.042927438
Topological Polar Surface Area:76.2
Heavy Atom Count:10
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes