64113-91-3, These common heterocyclic compound, 64113-91-3, name is tert-Butyl 2-aminobenzoate, its 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.
A 12 L round bottom flask, equipped with a thermocouple, nitrogen adapter and a 1 L addition funnel, was charged with a solution [OF T-BUTYL 2-AMINOBENZOATE] (537g, 2.78 moles; lot 36648-tjb-40) in ethanol (1620 [ML,] 3 ml/g). To this golden solution was added water (615.6 [ML)] resulting in a biphasic mixture. This mixture was cooled to between 15 and 20 C with a cold-water bath. A 1.0 M solution of [ICL IN CHZCIZ] [(ALDRICH LOT #14127JO,] 3.11 L, 3.11 moles, 1.12 equiv. ) was charged in portions to the addition funnel and was added to the rapidly stirred mixture maintaining the temperature between 15 and [25 C.] The addition time was 2.25 hours and the temperature range observed was 16.5 to 20. [4 C.] The resulting red brown mixture was stirred at room temperature for 1 hour at which time the GC assay showed the reaction was complete. The reaction was diluted with 920 mL of water and quenched with 456 mL of [38%] aq. sodium bisulfite (Webb [CHEM LOT #10464519)] resulting in a slight exotherm to 24. [0 C.] This mixture was stirred for 15 minutes before separating the phases. The methylene chloride layer was combined with water (3.7L) and stirred for 15 minutes before separating the phases. A [NAOH] solution was prepared by diluting 10% [NAOH] [(460ML)] in water (2.3L). To the methylene chloride layer was added this dilute [NAOH] solution (2.1L). The pH of the basic phase was 6.56. The phases were separated and the methylene chloride layer was concentrated to a low volume in vacuo at 16 torr using a bath temp of [45 C. PYRIDINE] (4L) was added, and the resulting solution was concentrated to ca. 1.0 mL/g [IN.] vacuo at 16 torr using a [62 C] water bath. The low volume pyridine/product mixture was diluted with pyridine to the target volume of 3. 1L (3. [5 ML/G).] A sample [(LOML)] was concentrated removing the pyridine on the rotovap and high vacuum to yield 3.12 g of an orange brown solid of 96% potecy by GC. GC assay of pyridine solution indicated that neither EtOH nor methylene chloride were present, so the solution was taken on directly into the next step.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 64113-91-3.
Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
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