ChemicalBook CAS DataBase List 6-bromoquinolin-8-amine

6-bromoquinolin-8-amine synthesis

4synthesis methods

Product Name:6-bromoquinolin-8-amine
CAS Number:57339-57-8
Molecular formula:C9H7BrN2
Molecular Weight:223.07

68527-67-3
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Yield:57339-57-8 91%

Reaction Conditions:

with iron;acetic acid in ethanol;water; for 3 h;Heating / reflux;

Steps:

49 INTERMEDIATE 49 6-Bromo-8-amino-quinoline

To a solution of 6-bromo-8-nitro-quinoline (4 g, 1.58 mmol) in EtOH/HOAc/H2O (50 mL/50mL/25mL) was added iron metal (3.18 g, 5.69 mmol). The resulting solution was heated at reflux for 3 hours. The cooled reaction mixture was neutralized with 2.5 N NaOH, filtered through celite to remove iron solids and washed with EtOAc. The eluent was extracted into EtOAc (3 x 200 mL), combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexanes) affording 3.19 g (91%) of a yellow solid: mp 142-145°C.

References:

EP1147083,2004,B1 Location in patent:Page 46

875-51-4 Synthesis