Methyl 3,4-diaMino-5-nitrobenzoate synthesis

Yield:54226-23-2 80%

Reaction Conditions:

palladium 10% on activated carbon in methanol;cyclohexane; for 0.5 h;Heating / reflux;

Steps:

204 Description 204; Methyl 3, 4-DIAMINO-5-NITROBENZOATE (D204)

To a solution of methyl 4-amino-3,5-dinitrobenzoate (D203) (3.0 g, 12.4 mmol, 1 equiv) in MEOH (40 mi) and cyclohexane (80 mi) was added 10% palladium on charcoal (50% wet, 2.0 g, 33% W/W) and the resulting mixture was refluxed for 30 min then cooled to room temperature. The catalyst was filtered off through a pad of celite and washed with DMF. The combined organic phases were concentrated in vacuo and the residue triturated with ET20/ISO- hexane to give methyl 3,4-diamino-5-nitrobenzoate (D204) (2.1 g, 80%) as a red solid which was used in the next step without further purification. [M+H] + = 212.2, RT = 2.46 min.

References:

WO2004/50619,2004,A1 Location in patent:Page 57