Electric Literature of 58677-05-7,Some common heterocyclic compound, 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, molecular formula is C10H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A solution ofethyl 2-nitrobenzoate (917 mg, 4.7 mmol) in MeOH (20 mL) and CH3COOH(0.1 mL) was subjected to two cycles N2/vacuum. Pd(OH)2/C10% wt (66 mg, 0.01 eq.) was added and the reaction mixture stirred at roomtemperature under H2 (1 atm) for 12 h. Propanal (337 muL, 4.7 mmol)and Pd(OH)2/C 10% wt (66 mg, 0.01 eq.) were added, and the reactionstirred at room temperature under H2 (1 atm) for additional 12 h.The suspension was filtered through Celite washing twice with CH2Cl2(20 mL). The solution recovered was evaporated under reduced pressure giving anoil after purification by flash chromatography (PE/AcOEt: 4/1). The oil obtained(1 eq.) was dissolved in dry CH2Cl2, and ethyl malonyl chloride(1 eq.) was added. The reaction mixture was stirred at room temperature under N2overnight. The reaction mixture was diluted with CH2Cl2and washed with a saturated solution of NaHCO3. Organic layers werethen washed with brine, dried over dry Na2SO4, filteredand evaporated under reduced pressure giving the expected compound after flashchromatography purification.
The synthetic route of 58677-05-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Manetti, Fabrizio; Petricci, Elena; Gabrielli, Annalisa; Mann, Andre; Faure, Helene; Gorojankina, Tatiana; Brasseur, Laurent; Hoch, Lucile; Ruat, Martial; Taddei, Maurizio; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 747 – 757;,
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