N-substituted Lactams by Ullmann Coupling of Aniline
AP 01 – 17 – 300 309
Chemicals [CAS] | Chemicals | MW [g/mol] | Density [g/mL] | Amount [mmol] | Mass / Volume |
675-20-7 | d-Valerolactam | 99.13 |
| 5.04 | 500 mg |
540-37-4 | 4-Iodoaniline | 219.02 |
| 4.2 | 920 mg |
7778-53-2 | K3PO4 | 212.27 |
| 8.4 | 1780 mg |
7681-65-4 | CuI | 190.45 |
| 0.21 | 40 mg |
108-00-9 | N,N’-Dimethylethylenediamine | 88.15 | 0.807 | 0.42 | 37 mg / 45 µL |
108-88-3 | Toluene | 92.14 | 0.867 | solvent | 10 mL |
Keywords | Lactams, Ullmann coupling, copper catalysis
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Instrument | Monowave 300 |
Description | A G30 vial was charged with the halogenated aniline, 1.2 equiv lactam, 5 mol% CuI, 10 mol% DMEN and 2 equiv K3PO4. All reagents were suspended in 10 mL dry toluene and the mixture was subjected to microwave radiation. |
Workup | After cooling the crude mixture was purified by column chromatography utilizing ethyl acetate/methanol. |
Comments | General protocol works also with 4-O and 4-S lactams in high yields. Subsequent functionalization at the amino group leads to a variety of potentially active lactam derivatives. |
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References | N. E. Núñez-Navarro et al., J. Braz. Chem Soc. 2017, 28, 203-207 |
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