Propanal → HCID 16081264, compound

Participants

Reaction Steps

Sodium cyanoborohydride (0.63 g) was added to a solution of 4-iodoaniline (2.2 g) and propionaldehyde (0.72 ml) in methanol (15 ml) whilst under an atmosphere of argon. The mixture was stirred at ambient temperature for 72 hours. Sodium cyanoborohydride (0.005 mole) was added and the reaction mixture was stirred for further 48 hours. The pH of the reaction mixture was adjusted to 1 using 2N aqueous hydrocyloric acid. The mixture was filtered and the filtrate was evaporated to yield N-propyl-4-iodoaniline as a solid (1.4 g), NMR: 0.9(3H,t), 1.65(2H,m), 3.1(2H,m), 7.05(2H,d) and 7.67(2H,d).

Provenance & Evidence