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ChemicalBook CAS DataBase List 2-AMINO-5-BROMONICOTINAMIDE

2-AMINO-5-BROMONICOTINAMIDE synthesis

3synthesis methods
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Yield:58483-98-0 80%

Reaction Conditions:

with ammonium chloride;benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;triethylamine in N,N-dimethyl-formamide at 25;

Steps:

15.1 Synthesis of2-amino-5-bromonicotinamide

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4C1 (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentratedin vacuo, suspended in water and extracted with CH2C12. The organic layer was washed with brine,dried over Na2504 and concentrated to give the product of 2-amino-5-bromonicotinamide (1.80 g,yield: 80%), which was used for the next step without further purification. ‘H NMR (DMSO-d6,400 MHz) 8.14 (dd, J= 4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H):216/218.

References:

WO2014/205593,2014,A1 Location in patent:Page/Page column 55