Potassium Iodide → HCID 23325020, compound

Participants

Reaction Steps

5-Amino-2-[4-aminobutyl]-3-methylpyridine (2.17 g) in 20% sulphuric acid (25 ml) at -5° C. was reacted with a solution of sodium nitrite (1 g) in water (5 ml) over 20 minutes. After a further 15 minutes at -9° C. the reaction mixture was added to a mixture of potassium iodide (4 g) and cuprous iodide (0.5 g) in water (65 ml) at 10° C. and then stirred at room temperature for 30 minutes. Saturated sodium thiosulphate solution (10 ml) was added and the pH was brought to 12 with sodium hydroxide. Chloroform extraction of the reaction mixture gave 5-iodo-3-methyl-2-(4-aminobutyl)pyridine as a dark oil (2.45 g). N.M.R. (CDCl3) assignment, δ (p.p.m.), multiplicity; (CH2)2CH2NH2, 1.4-2.0, m; NH2, 1.69, s; 3--CH3, 2.28, s; CH2 (CH2)2CH2NH2, 2.76, m; 4--H pyridyl, 7.75, m; 6--H pyridyl, 8.57, m.

Provenance & Evidence