Ammonia → 2-Pyrrolidinone, 1-(8-quinolinyl)-

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Reaction Steps

A mixture of 1-(2-aminophenyl)-2-pyrrolidinone (J. Chem. Soc. C, 1969 (10), 1444-8) (3.2 g, 0.018 mole) and arsenic (V) oxide (2.5 g, 0.011 mole) in aqueous sulphuric acid (concentrated sulphuric acid (4.0 ml) in water (1.3 ml)) was heated to 70° and stirred vigorously. Acrolein (2.5 ml, 0.037 mole) was added dropwise at a rate such that the reaction temperature did not exceed 95°. The reaction temperature was maintained at 95° to 115° by heating and stirring in a nitrogen atmosphere for 1 hour after addition of acrolein was complete. The product was poured into water and the pH was adjusted to pH 6 with concentrated ammonia. Extraction of the aqueous solution with methylene chloride, after removal of the solvent, afforded an oil. Separation was achieved by column chromatography (200 g SILICA GEL 60 (Trade Name)). The oil was eluted first with acetone/ethyl acetate (30:70) then acetone/ethyl acetate (50:50) and finally acetone. The solvet was removed from the acetone/ethyl acetate (50:50) and the acetone fractions to afford a homogeneous solid as shown by tlc analysis. Crystallization from acetone afforded 1-(8-quinolyl)-2-pyrrolidinone (m.p. 121° -122°), yield 21%. Analysis of the sample by tlc and NMR as well as elemental analysis verified the identity of this material with that obtained in Example 1.

Provenance & Evidence