Toluene → Methyl 3-amino-4-(methyloxy)-5-nitrobenzoate

Participants

Reaction Steps

To a solution of methyl 4-(methyloxy)-3,5-dinitrobenzoate (D25) (5.0 g, 19.5 mmol, 1 equiv) in AcOH (150 ml) at room temperature was added iron powder (9.0 g, 161 mmol, 8.2 equiv) portionwise and the resulting mixture was stirred for 3 h. Toluene (500 ml) was added and the organic phase was filtered through a pad of celite then concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Trituration of the residue with Et2O/iso-hexane gave methyl 3-amino-4-(methyloxy)-5-nitrobenzoate (D163) (3.65 g, 83%) as a yellow solid which was used in the next step without further purification. [M+H]+=226.9, RT=2.76 min.

Provenance & Evidence