7-AMINO-1,8-NAPHTHYRIDIN-2(8H)-ONE Chemical Properties

Melting point:

>335°C (dec.)

Boiling point:

415.6±38.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Methanol (Slightly, Heated)

form 

Solid

pka

3.39±0.20(Predicted)

color 

Dark Yellow to Yellow-Brown

InChI

InChI=1S/C8H7N3O/c9-6-3-1-5-2-4-7(12)11-8(5)10-6/h1-4H,(H3,9,10,11,12)

InChIKey

NSPQTGOJGZXAJM-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C(N)N=2)C=CC1=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

7-AMINO-1,8-NAPHTHYRIDIN-2(8H)-ONE Usage And Synthesis

Uses

2-Amino-7-hydroxy-1,8-naphthidine is used as a research compound and in organic synthesis, etc.

Chemical Properties

Yellow-Brown Solid

Synthesis

2,6-diaminopyridine (20 g, 0.18 mol) and DL-malic acid (27 g, 0.2 mol) were used as raw materials in a 500 mL three-necked round-bottomed flask equipped with a dosing funnel, thermometer and mechanical stirrer. The mixture was cooled in an ice-water bath, and concentrated sulfuric acid (100 mL) was added slowly dropwise, with the rate of dropwise acceleration controlled to keep the reaction temperature from exceeding 45 °C. Subsequently, the addition funnel was replaced with a reflux condenser and the reaction mixture was heated to 110°C and maintained for 3 hours. Upon completion of the reaction, the solution was transferred to a 1 L beaker, cooled to 0 °C via an ice-water bath, and adjusted to pH=8 by slowly adding aqueous NH4OH (300 mL).The crude product was collected by vacuum filtration and the filter cake was washed with 2 L of water. The solid product was ground with a 1:9 (v:v) water:methanol mixture and collected again by vacuum filtration to afford 7-amino-2-hydroxy-1,8-diazanaphthalene as a tan powder in 25 g (86% yield). The product was structurally confirmed by 1H NMR (500 MHz, DMSO-d6) and 13C NMR (126 MHz, DMSO-d6) as well as mass spectrometry (ESI, CH3OH).

References

[1] Journal of Organic Chemistry, 1981, vol. 46, # 5, p. 833 - 839
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 13, p. 2578 - 2589
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4899 - 4906
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 1, p. 90 - 95
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 33, p. 6500 - 6506

7-AMINO-1,8-NAPHTHYRIDIN-2(8H)-ONE(1931-44-8)Related Product Information

• 1,8-NAPHTHYRIDIN-2(8H)-ONE
• AURORA KA-3607
• 2-(7-AMINO-2-HYDROXY[1,8]NAPHTHYRIDIN-4-YL)-ACETIC ACID
• 7-AMINO-1,8-NAPHTHYRIDIN-2(1H)-ONE SULFATE
• AURORA KA-3603
• 7-AMINO-1,8-NAPHTHYRIDIN-2(8H)-ONE
• 7-(dimethylamino)-4-methoxy-1-methyl-1,8-naphthyridin-2(1H)-one
• 2-HYDROXY-7-N-PHTHALIMIDYL-1,8-NAPHTHYRIDINE
• 7-AMINO-2-HYDROXY-1,8-NAPHTHYRIDINE-4-CARBOXYLIC ACID
• 7-AMINO-4-METHYL-1H-[1,8]NAPHTHYRIDIN-2-ONE
• 7-amino-4-methyl-1,8-naphthyridin-2-ol