Methyl iodide → N-Boc 4-Iodo-N-methylaniline

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Procedure

A solution of N-tertiary-butyloxycarbonyl-4-iodoaniline (11.5 g, see P G Ciattini et al, Tet. Lett, 1995, 36, 4133-4136 for preparation) in dimethylformamide (70 mL), under nitrogen, was treated portionwise with sodium hydride (1.6 g, 60% dispersion in mineral oil). When effervescence had ceased (after about 5 minutes) the mixture was treated with methyl iodide and stirring was continued at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate (500 mL) and water (500 mL). The organic phase was dried and then evaporated to give the title compound (11.5 g) as a pink oil.