Iodoethane → HCID 69356918, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3,4-diamino-5-nitrobenzoate (D204) (1.5 g, 7.1 mmol, 1 equiv) in DMF (30 ml) at room temperature was added K2CO3 (2.2 g, 16.0 mmol, 2.25 equiv) then ethyl iodide (1.28 ml, 16.0 mmol, 2.25 equiv). The resulting suspension was stirred at 60° C. for 2 h then ethyl iodide (1 ml, 12.5 mmol, 1.8 equiv) was added and the resulting mixture stirred for another 6 h then cooled to room temperature and partitioned between AcOEt and a saturated aqueous NaHCO3 solution. The two layers were separated and the organic phase washed with H2O, dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give methyl 4-amino-3-(ethylamino)-5-nitrobenzoate (D205) (0.85 g, 50%) as a red solid which was used in the next step without further purification. [M+H]+=240.2, RT=2.95 min.

Provenance & Evidence