6-Hydroxyquinoline synthesis
- Product Name:6-Hydroxyquinoline
- CAS Number:580-16-5
- Molecular formula:C9H7NO
- Molecular Weight:145.16
Yield:580-16-5 77%
Reaction Conditions:
with sulfuric acid in water at 220; for 0.166667 h;Microwave irradiation;Green chemistry;regioselective reaction;Skraup Quinoline Synthesis;Temperature;Reagent/catalyst;Concentration;
Steps:
2.3 Typical procedure for the modified Skraup reaction
A 30mL sealed vessel was charged with nitrobenzene (3, 10mmol), glycerol (1, 40mmol, 4.0eq), H2SO4 (30mmol, 3eq) in water (7.4mL). The mixture was irradiated with a power high enough to reach the predicted temperature with a heating ramp of 7°C·min-1, then 220°C for 10min. After cooling at room temperature, pH was adjusted at 8-9 by addition of NaOH and the reaction mixture was extracted with ethyl acetate (3×20mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by column chromatograph (cyclohexane/EtAc, 1:1, v/v) on silica gel yielding the 6-hydroxyquinoline (5, 1.12g, 77%).
References:
Saggadi, Hanen;Luart, Denis;Thiebault, Nicolas;Polaert, Isabelle;Estel, Lionel;Len, Christophe [Catalysis Communications,2014,vol. 44,p. 15 - 18]
612-57-7
221 suppliers
$6.00/1g
580-16-5
237 suppliers
$5.00/1g
