Table 1.

Copper-catalyzed amination of 2-chlorobenzoic acid^a

entry	catalyst (mol %)	reaction time (h)	yield (%)b
1	CuI (4%)	24	55
2	Cu2O (4%)	24	56
3	Cu (9%)	24	55
4	Cu (9%), CuI (4%)	24	51
5	Cu (9%), Cu2O (4%)	24	76
6	Cu (12%), Cu2O (4%)	5	66
7	Cu (9%), Cu2O (4%)	5	71
8	Cu (6%), Cu2O (4%)	5	51
9	Cu (4%), Cu2O (4%)	5	51

^aReaction conditions: 2-Chlorobenzoic acid (1.38 g, 8.83 mmol), 1.05 equiv. of 2-methylaniline, 2.0 equiv. of potassium carbonate in 3 mL of 2-ethoxyethanol at 130°C.

^bIsolated yields.