Methyl iodide → 6-Nitro-o-anisidine

Participants

Reaction Steps

To a stirred solution of 20 g (129.9 mmol) 2-hydroxy-6-nitroaniline in 150 ml DMF, NaH (3.42 g, 143 mmol, 95%) is added at 0° C. and stirring is continued for 1.5 h. MeI (9.3 ml, 150 mmol) is added and the reaction mixture is stirred at room temperature for 1 h. After that the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. To the residue 50 ml of hexane:diethyl ether=4:1 is added and the resulting suspension is stirred for 5 minutes. 20 g of the title compound are obtained after filtration of the mixture as a brown crystalline solid.

Provenance & Evidence