[7521-41-7] C₆H₆N₂O (MW 122)

InChI = 1S/C6H6N2O/c7-6-5(4-9)2-1-3-8-6/h1-4H,(H2,7,8)

InChIKey = NXMFJCRMSDRXLD-UHFFFAOYSA-N

(1,8-naphthyridine synthesis; Friedländer synthon; β-amino aldehyde)

Alternate Name: 2-amino-3-pyridinecarbaldehyde.

Physical Data: yellow solid, sublimes readily, mp 98–99 °C.

Solubility: ether, ethyl acetate: good; dichloromethane: poor.

Preparative Methods: 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.²

Handling, Storage, and Precautions: the reagent 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.