ETHYL 2-AMINO-5-BROMONICOTINATE

ETHYL 2-AMINO-5-BROMONICOTINATE Property

Melting point:

139-141°

Boiling point:

290.6±35.0 °C(Predicted)

Density 

1.575±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.59±0.49(Predicted)

Appearance

Light yellow to yellow Solid

Safety

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

ETHYL 2-AMINO-5-BROMONICOTINATE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of ethyl 2-amino-5-bromonicotinate from ethyl 2-aminonicotinate: to a stirred solution of ethyl 2-aminonicotinate (15 g; 90.36 mmol; 1 eq.) in anhydrous THF (150 mL) was added N-bromosuccinimide (NBS) (16 g; 90.36 mmol; 1 eq.) in batches at 0 °C. The resulting mixture was stirred at 23 °C for 18 hours. Upon completion of the reaction, the mixture was poured into ice-cold saturated aqueous NaHCO3 solution and the organic components were extracted with ethyl acetate (3 x 200 mL). The combined organic layers were washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure to afford ethyl 2-amino-5-bromonicotinate (22 g, 100%) as an off-white solid. The product was confirmed by 1H NMR (DMSO-d6): δ 8.29 (d, 1H, J = 3Hz), 8.12 (d, 1H, J = 2Hz), 7.31 (s, 2H), 4.29 (q, 2H, J = 7Hz), 1.30 (t, 3H, J = 7Hz).The LCMS analysis resulted in: m/z = 245.0 [M + H]+, 247.0 [M + 2H]+, retention time (RT) = 3.34 min (program P1, column W).

References

[1] Patent: WO2015/95128, 2015, A1. Location in patent: Paragraph 0239; 0242; 0243
[2] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 236 - 246
[3] Patent: CN104402881, 2016, B. Location in patent: Paragraph 0022; 0023
[4] Patent: WO2007/67416, 2007, A2. Location in patent: Page/Page column 64; 134