N-substituted Lactams by Ullmann Coupling of Aniline

AP 01 – 17 – 300 309

Chemicals [CAS]

Chemicals
 (Name)

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

 

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.

 

 

References

N. E. Núñez-Navarro et al., J. Braz. Chem Soc. 2017, 28, 203-207

Get the document

To receive this document please enter your email below.

Loading...

Error