2-AMINO-6-BROMO-1,8-NAPHTHYRIDINE Chemical Properties

Melting point:

210-212 °C (sublm)

Boiling point:

357.2±37.0 °C(Predicted)

Density 

1.744±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

4.15±0.30(Predicted)

Appearance

Light yellow to orange Solid

Safety Information

Risk Statements 

41

Safety Statements 

26-39

HS Code 

2902900000

2-AMINO-6-BROMO-1,8-NAPHTHYRIDINE Usage And Synthesis

Uses

6-Bromo-1,8-naphthyridin-2-amine is used as a reactant in the preparation of substituted naphthyridines as H-PGDS inhibitors.

Synthesis

General procedure for the synthesis of 2-amino-6-bromo-1,8-naphthyridine from 2,6-diaminopyridine and 2-bromomalonaldehyde: 2,6-diaminopyridine (6.0 g, 55 mmol) and 2-bromo-1,3-malonaldehyde (8.0 g, 53 mmol) were dissolved in 85% orthophosphoric acid (160 mL) and heated and refluxed for 6 hours. Upon completion of the reaction, the reaction endpoint was confirmed by thin layer chromatography (TLC) monitoring. After cooling the reaction mixture to room temperature, it was neutralized with ammonia (NH4OH) solution to give a dark brown solid. After filtration and drying of this solid, it was dissolved in methanol (MeOH) with the aid of sonication. Purification by column chromatography afforded the light yellow solid product 2-amino-6-bromo-1,8-naphthyridine (3.85 g, 30.3% yield), which had an Rf value of 0.39 (unfolding reagent ratio CH2Cl2:MeOH = 10:1) and a melting point of 160-162°C (literature value 4: 210-212°C). The 1H NMR (500 MHz, DMSO-d6) data of the product were as follows: δ 7.82 (d, J = 2.6 Hz, 1H), 7.46 (d, J = 2.6 Hz, 1H), 7.04 (d, J = 8.8 Hz, 1H), 6.14 (s, 2H), 5.99 (d, J = 8.8 Hz, 1H).

References

[1] Heterocycles, 2015, vol. 91, # 5, p. 1001 - 1006

2-AMINO-6-BROMO-1,8-NAPHTHYRIDINE(64874-38-0)Related Product Information

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