4-BUTYLAMINO-3-NITRO-BENZOIC ACID synthesis
- Product Name:4-BUTYLAMINO-3-NITRO-BENZOIC ACID
- CAS Number:120321-65-5
- Molecular formula:C11H14N2O4
- Molecular Weight:238.24
Yield:120321-65-5 70%
Reaction Conditions:
with sodium hydrogencarbonate in water at 150; for 3 h;
Steps:
4-(butylamino)-3-nitrobenzoic acid (5a)
General procedure: Following a procedure adapted from Skinner et al.,30 4-fluoro-3-nitrobenzoic acid (~1 mmol) (3a), NaHCO3 (2.1 mol eq), and N-butylamine (2.2 mol eq) were dissolved in 3 mL of water in a heavy walled reaction vessel. The reaction was heated to 150 °C and stirred for 3 h. The reaction was cooled to room temperature and 20 mL of 1 M HCl was added to the reaction. The mixture was dissolved in approximately 20 mL ethyl acetate, washed with water (2 x 15 mL) and brine (1 x 15 mL). The organic layer was dried over magnesium sulfate, filtered, removed in vacuo, and subsequently purified via column chromatography to yield 5a (70%).
References:
Kirk, Sarah R.;Jackson, Evan P.;Cuellar, Elysia;Andrade, Adriana L.;Melich, Kenneth;Karpen, Jeffrey W. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 21,p. 6417 - 6419] Location in patent:supporting information; experimental part
