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Summary and Conclusion
Reaction proceeded as expected. Final isolated yield following recrystallisation, 7.1 g (92%).
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START: 07/05/12.
FINISH: 08/05/12
Repeat of KAB23-1. Preparation of additional starting material.
Hazard and Risk Assessment
As for KAB23-1
Previous Experiments
Synthesis of 2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (KAB23-1)
Following Experiments
Chemical Information
3,4-Dimethoxyphenethylamine - SMILES: O(c1ccc(cc1OC)CCN)C, InChI: InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3, InChIKey: ANOUKFYBOAKOIR-UHFFFAOYSA-N.
4-Nitrobenzaldehyde- SMILES: O=C([H])C1=CC=C([N+]([O-])=O)C=C1, InChI: InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H, InChIKey: BXRFQSNOROATLV-UHFFFAOYSA-N.
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
4-Nitrobenzaldehyd (3.7 g, 23.5 mmol, 1 equiv.) was suspended in diethyl ether (50 mL) before the addition of 3,4-dimethoxyphenethylamine (4.0 mL, 24.5 mmol, 1 equiv.). The reaction mixture was left to stir at rt from 09:20. After 6 hours, the reaction mixture was concentrated under reduced pressure to give a light yellow solid (7.95 g, 103%). The crude product was recrystallised from hot ethanol (~200 mL) and left to stand overnight. The crystals were filtered and washed with EtOH then dried under a high vacuum to give KAB23-2 as yellow needles (7.1 g, 23 mmol, 92%).
Summary and Conclusion
Reaction proceeded as expected. Final isolated yield following recrystallisation, 7.1 g (92%).
References
[1] R. Gitto, M. L. Barreca, L. De Luca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, A. Chimirri, Journal of Medicinal Chemistry 2003, 46, 197.
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NOTES 07/05/12
- Flask - 159.23
- Jar -
-----------------------------------------------------------------------------
Summary and Conclusion
Reaction proceeded as expected. Final isolated yield following recrystallisation, 7.1 g (92%).
-------
START: 07/05/12.
FINISH: 08/05/12
Repeat of KAB23-1. Preparation of additional starting material.
Hazard and Risk Assessment
As for KAB23-1
Hazard and Risk Assessment KAB23-1
Previous Experiments
Synthesis of 2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (KAB23-1)
Following Experiments
Chemical Information
3,4-Dimethoxyphenethylamine - SMILES: O(c1ccc(cc1OC)CCN)C, InChI: InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3, InChIKey: ANOUKFYBOAKOIR-UHFFFAOYSA-N.
H-NMR (MeO)2PEA
H-NMR (MeO)2PEA
4-Nitrobenzaldehyde- SMILES: O=C([H])C1=CC=C([N+]([O-])=O)C=C1, InChI: InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H, InChIKey: BXRFQSNOROATLV-UHFFFAOYSA-N.
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
4-Nitrobenzaldehyd (3.7 g, 23.5 mmol, 1 equiv.) was suspended in diethyl ether (50 mL) before the addition of 3,4-dimethoxyphenethylamine (4.0 mL, 24.5 mmol, 1 equiv.). The reaction mixture was left to stir at rt from 09:20. After 6 hours, the reaction mixture was concentrated under reduced pressure to give a light yellow solid (7.95 g, 103%). The crude product was recrystallised from hot ethanol (~200 mL) and left to stand overnight. The crystals were filtered and washed with EtOH then dried under a high vacuum to give KAB23-2 as yellow needles (7.1 g, 23 mmol, 92%).
Stirring aldehyde suspension
After the addition of (MeO)2PEA
Reaction mixture (3 h)
KAB23-2 recrystallisation
KAB23-2
Summary and Conclusion
Reaction proceeded as expected. Final isolated yield following recrystallisation, 7.1 g (92%).
References
[1] R. Gitto, M. L. Barreca, L. De Luca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, A. Chimirri, Journal of Medicinal Chemistry 2003, 46, 197.
-----------------------------------------------------------------------------
NOTES 07/05/12
- Flask - 159.23
- Jar -
-----------------------------------------------------------------------------
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Scheme KAB23-2
Stirring aldehyde suspension
After the addition of (MeO)2PEA
Reaction mixture (3 h)
KAB23-2 recrystallisation
KAB23-2