Hydrochloric Acid → Quinoline

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL 3-neck flask fitted with condenser, addition funnel and a thermometer was added 10.0 g of 2-Amino-4-tert-butylphenol (Aldrich) dissolved in 50.0 mL acetic acid. To the solution was added 3.90 g of 4-(t-butyl)-2-nitrophenol (Aldrich) and 100 mL of concentrated HCl. The contents of the flask were heated to 80° C. by means of an oil bath. Acrolein (Aldrich) (6.78 g) was added over 30 min via the addition funnel. After the addition was complete, the solution was heated to 130° C. for 16 hrs. The solution was allowed to cool to room temperature and then poured into 300 mL cold water and neutralized to pH7.0 by addition of a 25% NaOH solution. A tan precipitate formed which was extracted from the aqueous solution (3×200 ml methylene chloride). The combined extracts were dried with MgSO4 and concentrated to an oil. The oil was resuspended in methylene chloride and the insoluble materials (unreacted 2-amino-4-tert-butylphenol) filtered off. The filtrate was concentrated to an oil and purified by chromatography on silica gel column eluting with 1:1 chloroform:hexanes to remove the non-polar impurities followed by chloroform to elute the product. The product containing fractions were combined and concentrated to an oil which solidified upon standing. Yield 1.56 g (13%)

Provenance & Evidence