Chemical Properties
yellow crystals
Uses
2-Aminonicotinaldehyde is commonly employed as a starting material for a wide variety of N-heterocyclic compounds (e.g. β-nicotyrine [N445000]) . 2-Aminonicotinaldehyde is also used as a reagent to synthesize hydrazones (e.g.thionaphthenquinone 3-hydrazone [T367720]), which possess antituburcular properties.
Preparation
Preparative Methods of 2-Amino-3-pyridinecarboxaldehyde: the reagent is best when freshly prepared. A multistep procedure starting from 2-amino-3-
picoline has been improved upon by a simple two-step approach. Sulfamation of nicotinamide with ammonium
sulfamate (both commercially available) provides 2-(3′-pyridyl)pyrido[2,3-d]pyridimine which may be
hydrolyzed in 2 N HCl to provide the reagent (eq 1)
[1]. Substituted derivatives of the reagent may be prepared via
a similar intermediate.
storage
2-Amino-3-pyridinecarboxaldehyde is somewhat more stable than 2-Aminobenzaldehyde and may
be stored for up to several months at 0 °C under an inert atmosphere. Sublimation is a convenient method for the
separation of higher oligomers which may accumulate during storage. Use in a fume hood.
References
1. (a) Caluwe, P. T 1980, 36, 2359. (b) Cheng, C.-C.; Yan, S.-J. OR 1982, 28, 37. (c) Thummel, R. P. SL 1992, 1.
