Insertion of the o-Aminophenol Core into Ninhydrin–Phenol Adducts: Migration of Ninhydrin Carbon Leading to N-Phenyl­benzoate-Substituted Phthalimides

Abstract

An unexpected migration of a ninhydrin carbon bearing a phenolic subunit has been observed when phenolic adducts of ninhydrin reacted with 2-aminophenol in butan-1-ol at the reflux temperature. The products were unambiguously assigned as 2-(1,3-dioxoisoindolin-2-yl)phenyl benzoates on the basis of NMR spectroscopy and X-ray crystallographic analysis.

Key words

phenols - rearrangement - heterocycles - migration - insertion

• References and Notes

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• 12 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl 2-Hydroxybenzoates 4a–g; General Procedure The appropriate ninhydrin adduct 2 (1.4 mmol) and 2-aminophenol (2.0 mmol) were added sequentially to BuOH (6 mL), and the mixture was refluxed for 3 h until the reaction was complete (TLC). The mixture was then cooled to r.t. and left overnight. The precipitated product was collected by filtration, washed with cold MeOH, and crystallized from acetone. 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl 2-Hydroxy-3-methoxybenzoate (4a) Light-yellow crystals; yield: 0.33 g (60%); mp 156–157 °C; IR (KBr): 3454, 3208, 1720, 1688 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 9.89 (s, 1 H), 7.94–7.91 (m, 2 H), 7.88–7.86 (m, 2 H), 7.64–7.58 (m, 3 H), 7.52–7.48 (m, 1 H), 7.24 (d, J = 8.0 Hz, 1 H), 7.17 (d, J = 7.8 Hz, 1 H), 6.75 (t, J = 8.0 Hz, 1 H), 3.76 (s, 3 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 166.2 (2 C), 165.4, 150.4, 148.3, 146.0, 134.9 (2 C), 131.3 (2 C), 130.1, 129.9, 126.6, 124.1, 123.9, 123.6 (2 C), 120.0, 118.8, 117.3, 112.8, 56.0. MS (ESI): m/z = 412 [M + Na]⁺, 279.1, 173.0. Anal. Calcd for C₂₂H₁₅NO₆ (389.37): C, 67.87; H, 3.88; N, 3.60. Found: C, 67.70; H, 3.97; N, 3.45.
• 13 CCDC 1566737 contains the supplementary crystallographic data for compound 4a. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
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