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ChemicalBook CAS DataBase List 3,8-DibroMo-6-nitroquinoline
696611-46-8

3,8-DibroMo-6-nitroquinoline synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

with pyridine;bromine in tetrachloromethane at 20; for 18 h;Heating / reflux;

Steps:

10.1.1 Stage 1: Preparation of 3-bromo-6-hydroxyquinoline and 3,8-dibromo-6-hydroxy-quinoline; Step 1: Preparation of 3-bromo-6-nitroquinoline and 3, 8-dibromo-6-nitroquinoline

In a modification of the procedure described in LIEBIGS ANN CHEM, (1966), 98-106 to make 3-bromo-6-nitroquinoline, 6-nitroquinoline (5. 5G) in carbon tetrachloride (200ML) containing pyridine (5. 0g) was treated with bromine (15.3g) and heated to reflux until all the 6-nitroquinoline had reacted. The reaction mixture was cooled to ambient temperature, stored for 18 hours then partitioned between chloroform and hydrochloric acid (2M). The mixture was filtered and the organic phase was separated, washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulphate then evaporated under reduced pressure to give a pale yellow solid. The solid was recrystallised from glacial acetic acid to give a mixture containing 3-bromo-6- nitroquinoline (4 parts) and 3,8-dibromo-6-nitroquinoline (1 part) as a pale yellow solid (4.06g).

References:

WO2004/47538,2004,A1 Location in patent:Page 55