✍ Scribed by Karen M. Button; Robert A. Gossage; Hilary A. Jenkins; Tayseer Mahdi; Sanja Resanović
No coin nor oath required. For personal study only.
magnified image The Lewis acid catalyzed synthesis and chromatographic purification of isatoic anhydride‐derived 2‐(2′‐anilinyl)‐1,3‐benzoxazole (2) can result in the co‐isolation of 2 and a light pink colored impurity (<5%). This latter species has been identified (NMR, single crystal X‐ray diffraction, mp) as 2′‐hydroxy‐2‐aminobenzanilide (3), which represents a predictable intermediate in the formation of 2. Compound 3 crystallizes in an orthorhombic crystal system of space group __P__2~1~2~1~2~1~ with four molecules in the unit cell (α = β = γ = 90°; a = 6.715 (2) Å, b = 12.100 (4) Å, c = 13.321 (4) Å; V = 1082.2 (6) Å^3^). Pure 2 is characterized as a colorless, high‐melting solid; unlike the dark colored oil that is isolated if 2 contains traces of 3. J. Heterocyclic Chem., (2010).
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## Abstract Substituted 2‐(benzylamino)‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones are unstable under alkaline and acidic conditions, undergoing opening of the benzoxazinone ring. 2‐Bromo‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones show similar degradation under alkaline conditions, while replacement of Br at C