Reactions of 2-chloromethylquinoline (1), its N-oxide (2) and their nitro derivatives with the sodium salt of 2-nitopropane were investigated. O-Alkylation occurred with 1 and 2, giving 2-quinolinecarboxyaldehyde (5 : 11%) and its N-oxide (6 : 10%). The reaction of 2-chloromethyl-5-nitroquinoline (3b) gave both the O-alkylation product, 5-nitro-2-quinolinecarboxyaldehyde (7 : 21%), and the C-alkylation products, 2-(2-methyl-2-nitropropyl)-5-nitroquinoline (8b : 24%) and 2-(2-methyl-1-propenyl)-5-nitroquinoline (9b : trace). In the reactions of the 6-nitro (3c) and 8-nitro (3d) derivatives of 1, the 2-(2-methyl-2-nitropropyl) quinolines (8c : 86% and 8d : 63%) were predominantly formed. In contrast, the reactions of the 4-nitro (4a), 5-nitro (4b) and 6-nitro (4c) derivatives of 2 produced the corresponding 2-(2-methyl-1-propenyl) quinoline N-oxides (11a : 53%, 11b : 20% and 11c : 66%) as main products, accompanied by small amounts of the 2-(2-methyl-2-nitropropyl) compounds (10a : 20% and 10b : 17%).