Sodium Carbonate → 2-Chloro-3-methoxyaniline

Participants

Reaction Steps

2-Chloro-3-nitroanisole 2C2 (1.38 g; 7.36 mmol) was dissolved in a mixture of glacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2(3×150 mL). The extracts were combined and washed with sat. brine and then dried over (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline 2C3 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps.

Provenance & Evidence