Conversion of N-aromatic amides to O-aromatic esters

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2349-2352

  Glatzhofer, Daniel T ^a   Roy, Raymond R ^a   Cossey, Kimberly N ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

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ARTICLE;

EID: 0041808014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026051d     Document Type: Article

References (29)

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2. Cohen, T.; Dietz, A. G., Jr.; Miser, J. R. J. Org. Chem. 1977, 42, 2053.
3. White, E. H. J. Am. Chem. Soc. 1954, 76, 4497.
4. White, E. H. J. Am. Chem. Soc. 1955, 77, 6008.
5. White, E. H. J. Am. Chem. Soc. 1955, 77, 6011.
6. White, E. H. J. Am. Chem. Soc. 1955, 77, 6014.
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8. White, E. H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 336.
9. White, E. H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 336.
10. White, E. H.; Dzadzic, P. M. J. Am. Chem. Soc. 1976, 98, 4020.
11. For other recent research concerning N-nitrosamide rearrangements, see: Darbeau, R. W.; Perez, E. V.; Sobieski, J. I.; Rose, W. A.; Yates, M. C.; Boese, B. J.; Darbeau, N. R. J. Org. Chem. 2001, 66, 5679 and references therein.
12. Norcross, B. E.; Becker, D.; Cukier, R. I.; Schultz, R. M. J. Org. Chem. 1967, 32, 220.
13. Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289.
14. Cipiciani, A.; Fringuelli, F.; Mancini, V.; Piermatti, O.; Pizzo, F.; Ruzziconi, R. J. Org. Chem. 1997, 62, 3744.
15. Falk, H.; Reich-Rohrwig, P.; Schlögl, K. Tetrahedron 1970, 26, 511.
16. The desired acetamide (1-3 mmol) is placed in a flask and dissolved in 15 mL of a 2:1 mixture of acetic anhydride and acetic acid. The flask is cooled to 0 °C in an ice bath. While the mixture is being slowly stirred magnetically, solid sodium nitrite (2 equiv, 1.6 equiv if the molecule has a nitrile group) is added to the mixture, and the vessel is lightly capped. Evolution of a brown gas occurs, the solution may change color, and sometimes a solid comes out of solution. The flask is kept in the ice bath for 2 h and allowed to warm to room temperature, where it is typically kept for 24 h, although the reaction may be complete much sooner. The solution may darken on standing. The mixture is poured into ice/water, and for solid samples, the resulting solid that forms is collected by suction filtration. Prolonged stirring is sometimes needed to sufficiently hydrolyze acetic anhydride, which can contribute to oil formation. Traces of acetic acid/anhydride can often be removed from the solid by dissolving in ethanol, pouring into ice/water, and collecting the resulting solid by suction filtration. The samples can be recrystallized from appropriate solvents as needed. For liquid or low melting point esters, the aqueous mixture from quenching the reaction is extracted with methylene chloride (3 × 50 mL). The combined methylene chloride extracts are washed with saturated sodium bicarbonate solution (3 × 50 mL) and dried using anhydrous magnesium sulfate. Methylene chloride is removed under reduced pressure to give the desired crude ester.
17. Literature mp's were taken from The Dictionary of Organic Compounds, 6th ed.; Chapman and Hall: New York, 1996 unless otherwise noted.
18. Unless otherwise noted, mass spectra were correlated with standard spectra available on the SDBS website. http://www.aist.go.jp/RIODB/SDBS/ (20Dec2001).
19. Ayres, D. C.; Levy, D. P. Tetrahedron 1986, 42, 4259.
20. Kimura, T.; Duan, X.; Kato, M.; Matsuda, H.; Fuduka, T.; Yamaca, S.; Okada, S.; Nakanishi, H. Mol. Cryst., Liq. Cryst. 1988, 164, 77.
21. Poirier, M.; Simard, M.; Wuest, J. D. Organometallics 1996, 15, 1296.
22. Cohen, T.; Deets, G. L. J. Org. Chem. 1972, 37, 55.
23. 16
24. Rylander, P. N. Hydrogenation Methods; Academic Press: Orlando, 1985; p 105.
25. 16
26. Bachman, W. E.; Hoffman, R. A. Org. React. 1944, 2, 224-261.
27. 2 under identical conditions. Each solution was added separately to test tubes containing 30 mL of methyl methacrylate (which had been filtered through neutral alumina to remove inhibitors and was shown not to contain polymer) each. Reaction and purification was carried out as above to give 0.227 g of polymer from the initiator containing the acetamide. Polymer was not obtained from the blank.
28. 16 showed that the sample contained 64% bibenzyl, 34% biphenyl, and 1% 4-biphenylacetate.
29. Kornblum, N. Org. React. 1944, 2, 262.