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9th April 2012 @ 23:32
START: 10/04/12 FINISH: [b][u]Background[/b][/u] Extending the reaction time. Also see synaptic leap post: [url=http://www.thesynapticleap.org/node/383]here[/url]. [b][u]Hazard and Risk Assessment[/b][/u] As for KAB24-1 ([url=http://www.ourexperiment.org/data/files/3784/HRA%20KAB24-1.pdf]here[/url]) [b][u]Previous Experiments[/b][/u] [blog]5127[/blog] [blog]5191[/blog] [blog]5183[/blog] [blog]5220[/blog] [blog]5304[/blog] [b][u]Following Experiments[/b][/u] [blog]5346[/blog] [b][u]Chemical Information[/u][/b] [b]2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (1, KAB23-1)[/b] - 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. [b]6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline (2, KAB24-3)[/b] - SMILES: O=[N+]([O-])C1=CC=C(C2NCCC3=CC(OC)=C(OC)C=C32)C=C1, InChi: InChI=1S/C17H18N2O4/c1-22-15-9-12-7-8-18-17(14(12)10-16(15)23-2)11-3-5-13(6-4-11)19(20)21/h3-6,9-10,17-18H,7-8H2,1-2H3, InChIKey: GITFNMZGMQLGOX-UHFFFAOYSA-N. [b][u]Procedure[/b][/u] KAB23-1 (313 mg, 996 mmol) was dissolved in toluene (30 mL) before the addition of trifluoroacetic acid (0.15 mL, 2.0 mmol, 2 equiv.) at rt. The reaction mixture was reflux heated to 110 °C from 9:45. [data]3885[/data][data]3929[/data] [b]Monitoring the Reaction Progress by TLC[/b] [data]3889[/data][data]3891[/data][data]3903[/data][data]3909[/data][data]3905[/data] [data]3927[/data] TLC at 5 min: Eluted with 5%, MeOH/DCM, v/v; ninhydrin stain. All other TLCs: Eluted with 15%, MeOH/DCM, v/v; ninhydrin stain. Diluted with EtOAc (30 mL) Quenched with saturated sodium bicarbonate (80 mL) Extracted with EtOAc (2 × 50 mL) Crude yield: 316 mg (101%). [b][u]Summary and Conclusion[/b][/u] [b][u]References[/b][/u] [1] R. Gitto, M. L. Barreca, L. De Luca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, A. Chimirri, [i]Journal of Medicinal Chemistry[/i] [b]2003[/b], 46, 197. ----------------------------------------------------------------------------- NOTES 10/04/12 - At 5 hours: reaction mixture contains both the suspected iminium ion and the cyclised product. NOTES 12/04/12 - Flask weight: 47.1237 g -----------------------------------------------------------------------------
Attached Files
Scheme KAB24-3
After the addition of TFA
TLC of reaction mixture (5 min)
TLC of reaction mixture (5 h)
TLC of reaction mixture (7 h)
TLC of reaction mixture (32 h)
TLC of reaction mixture (23 h)
TLC of reaction mixture (71 h)
Reaction mixture (72 h)