All Notebooks | Help | Support | About
This is a previous version of this entry. To view the latest click here. or to view all revisions click here.
9th May 2012 @ 06:15
START: 09/05/12


Hazard and Risk Assessment
Hazard and Risk Assessment KAB26-4

Previous Experiments
Yb(OTf)3 catalysed PS reaction to give 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB21-9)
TFA catalysed synthesis of 6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline (KAB24-4)
Lewis acid-catalyst screen for the PS reaction to give KAB21 and KAB24
AuCl3/AgOTf catalysed acyl-PS reaction to give 1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-1 & KAB26-2)
Preparation of the 2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine starting material (KAB23-2)

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.
1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-4) - SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N.

All glassware was ovendried overnight prior to use.
09/05/12. KAB23-1 (0.365 g, 1.161 mmol, 1 equiv.) was dissolved in freshly distilled MeCN (60 mL) before the sequential addition of well dried 3Å powdered MS, acetyl chloride (0.08 mL, 1.2 mmol, 1 equiv.) and 2,6-lutidine (0.13 mL, 1.161 mmol, 1 equiv.). Yb(OTf)3 (60 mg, 0.097 mmol, 10 mol%) was added and the reaction mixture was left to stir at rt, under argon from 18:00.

Summary and Conclusion

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

NOTES 04/05/12
Remaining fractions to be combined and concentrated first thign next week.
Linked Posts
Attached Files
Scheme KAB26-4
Hazard and Risk Assessment KAB26-4