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28th May 2012 @ 08:10
START: 28/05/12
FINISH:




Hazard and Risk Assessment
As for KAB26-2
HRA KAB26-X


Previous Experiments

Following Experiments

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (KAB23-2) - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N.

Procedure
28/05/12. A mixture of HAuCl3ยท3H2O (31 mg, 0.079 mmol, 1 mol%) and AgOTf (30 mg, 0.12 mmol, 2 mol%) in acetonitrile (15 mL) was vigorously stirred at room temperature from 17:10.
KAB23-2 (1.9 g, 6.1 mmol, 1 equiv.) was dissolved in acetonitrile (250 mL) before the sequential addition of acetyl chloride (0.40 mL, 6.1 mmol, 1 equiv.) and 2,6-lutidine (0.70 mL, 6.1 mmol, 1 equiv.). After the gold/silver mixture had stirred for 1 hour, the KAB23-1 mixture was added, and the reaction mixture was left to stir overnight, from 18:10.
29/05/12. After 14 hours, the reaction mixture was concentrated under reduced pressure.
F8-16 (aldehyde).
F50-68 Product (875 mg).

Summary and Conclusion
Isolated yield of KAB26-10 was 40% following silica gel column chromatography. By products of the reaction included 4-nitrobenzaldehyde and N-(3,4-dimethoxyphenethyl)acetamide.

References
[1] S. W. Youn, The Journal of Organic Chemistry 2006, 71, 2521-2523. DOI: 10.1021/jo0524775. Paper

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NOTES 28/05/12
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