Production Method 1

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  0 °C → 20 °C; 35 min, 20 °C
1.2 Reagents: Fuming nitric acid ;  4.5 h, < 5 °C

Reference

Process Development and Multikilogram-Scale Synthesis of a TRPV1 Antagonist

Cleator, Ed; Scott, Jeremy P.; Avalle, Paulo; Bio, Matthew M.; Brewer, Sarah E.; et al, Organic Process Research & Development, 2013, 17(12), 1561-1567

Production Method 2

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Nitric acid Solvents: Water ;  10 min, 80 °C

Reference

Synthesis and structure-activity relationships of pyrido[3,2-b]pyrazin-3(4H)-ones and pteridin-7(8H)-ones as corticotropin-releasing factor-1 receptor antagonists

Dzierba, Carolyn D.; Sielecki, Thais M.; Arvanitis, Argyrios G.; Galka, Amy; Johnson, Tricia L.; et al, Bioorganic & Medicinal Chemistry Letters, 2012, 22(15), 4986-4989

Production Method 3

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid
1.2 Solvents: Water

Reference

Structure-Activity Relationships of a Series of Pyrrolo[3,2-d]pyrimidine Derivatives and Related Compounds as Neuropeptide Y5 Receptor Antagonists

Norman, Mark H.; Chen, Ning; Chen, Zhidong; Fotsch, Christopher; Hale, Clarence; et al, Journal of Medicinal Chemistry, 2000, 43(22), 4288-4312

Production Method 4

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid ;  0 °C

Reference

Regioselective coupling reactions of 2,4-diaminopyridine derivatives with aryl halides: the synthesis of elaborated pyridines

Bio, Matthew M.; Cleator, Ed; Davies, Antony J.; Hamilton, Simon E.; Lawrence, Andrew; et al, Tetrahedron, 2009, 65(44), 8950-8955

Production Method 5

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Nitric acid

Reference

Imidazo[4,5-b]pyridines as corticotropin releasing factor receptor ligands

Arvanitis, Argyrios G.; Rescinito, Joseph T.; Arnold, Charles R.; Wilde, Richard G.; Cain, Gary A.; et al, Bioorganic & Medicinal Chemistry Letters, 2003, 13(1), 125-128

Production Method 6

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Nitric acid

Reference

1-Deazaadenine (7-aminoimidazo[b]pyridine). I. Deazapurine derivatives

Kogl, F.; van der Want, G. M.; Salemink, C. A., Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1948, 67, 29-44

Production Method 7

626-03-9

89282-12-2

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  30 min, 0 °C; 0.5 h, 0 °C
1.2 Solvents: Water ;  1 h, 0 °C

Reference

Scaffold morphing leading to evolution of 2,4-diaminoquinolines and aminopyrazolopyrimidines as inhibitors of the ATP synthesis pathway

Tantry, Subramanyam J.; Shinde, Vikas; Balakrishnan, Gayathri; Markad, Shankar D.; Gupta, Amit K.; et al, MedChemComm, 2016, 7(5), 1022-1032

Production Method 8

52809-57-1

89282-12-2

Reaction Conditions

1.1 Reagents: Nitric acid

Reference

Preparation of 2,4-dihydroxypyridine N-oxide

Talik, Tadeusz; Talik, Zofia, Prace Naukowe Akademii Ekonomicznej imienia Oskara Langego we Wroclawiu, 1985, 313, 115-19

3-Nitropyridine-2,4-diol Raw materials

• 4-hydroxy-1,2-dihydropyridin-2-one
• 2(1H)-Pyridinone, 4-hydroxy-3-nitroso-

3-Nitropyridine-2,4-diol Preparation Products

• 3-Nitropyridine-2,4-diol (89282-12-2)

• 1. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 2. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 3. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 4. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 5. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203

• Solvents and Organic Chemicals Organic Compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds C-nitro compounds
• Solvents and Organic Chemicals Organic Compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds Organic nitro compounds C-nitro compounds

• 18677-42-4(2,6-Dimethoxy-3,5-dinitropyridine)
• 96859-47-1(2,6-Dimethoxy-5-nitro-pyridin-3-ylamine)
• 607373-84-2(2,4-Dimethoxy-5-nitropyridine)
• 15990-90-6(2H-1-Benzopyran-2-one,8-[[bis(2-hydroxyethyl)amino]methyl]-7-hydroxy-4-methyl-, hydrochloride (1:1))
• 18617-40-8(Pyridine,2-methoxy-3,5-dinitro-)
• 31872-62-5(4-Methoxy-3-nitropyridine)
• 18677-41-3(2,6-Dimethoxy-3-nitropyridine)
• 20265-35-4(2-Methoxy-3-nitropyridine)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)