Ethylenediamine → HCID 58056094, compound

Participants

Reaction Steps

A suspension of 3-methoxy-4-nitro-benzoic acid (1.5 g, 7.61 mmol) in thionyl chloride (20 mL) and N,N-dimethylformamide (2 drops) was heated at reflux for 2 hours. The solvent was then evaporated under reduced pressure to give a light yellow solid. A portion of this residue (3.8 mmol) was dissolved in acetone (previously dried over anhydrous sodium sulfate) (20 mL) and cooled in an ice bath. Then a solution of ethylendiamine (0.46 mL, 7.62 mmol) in water (10 mL) was added at 0° C. and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between water and ethyl acetate; the aqueous phase was separated and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (EtOAc/MeOH, 100/0 to 98/2) to afford 0.42 g (46% 2 steps yield) of N-(2-hydroxy-ethyl)-3-methoxy-4-nitro-benzamide.

Provenance & Evidence