4-(Butylamino)-benzoic acid, methyl ester synthesis
- Product Name:4-(Butylamino)-benzoic acid, methyl ester
- CAS Number:71839-12-8
- Molecular formula:C12H17NO2
- Molecular Weight:207.27
Yield: 34%
Reaction Conditions:
with palladium on activated charcoal in tetrahydrofuran at 170; for 1.5 h;Microwave irradiation;
Steps:
N-Butylaniline (4)
General procedure: A 10-mL vial for MW equipped with a magneticstirrer was charged with Pd/C (10% wt, 106 mg, 0.1 mmol) under nitrogen. Dry THF (2 mL),aniline (1) (186 mg, 2 mmol) and N-butylamine (2) (73 mg, 1 mmol) were subsequently added. Themixture was stirred under MW dielectric heating for 90 min at 170 °C (max internal pressure 300psi). After cooling, the crude reaction mixture was filtered through a pad of celite and washed withMeOH. The collected solvent dried over anhydrous MgSO4 and further removed under vacuum.Purification by flash chromatography (petroleum ether 40-60/EtOAc 9:1) gave product 4 as a paleyellow oil (149 mg, yield 99%). The isolated product had the same spectroscopic features comparedwith reported data1 and was identical to an authentic sample (GC/MS analysis
References:
Linciano, Pasquale;Pizzetti, Marianna;Porcheddu, Andrea;Taddei, Maurizio [Synlett,2013,vol. 24,# 17,p. 2249 - 2254]
356100-70-4
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