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Catalog Number
ACM632340568
Product Name
2-(Bromomethyl)-3-nitrobenzoic acid
Structure
CAS
632340-56-8
Category
Heterocyclic Organic Compound
Description
2-(Bromomethyl)-3-nitrobenzoic acid is a chemical compound that is widely used in scientific research. It is a derivative of benzoic acid and contains a nitro group and a bromomethyl group. This compound has several applications in the fields of chemistry, biochemistry, and pharmacology.
2-(Bromomethyl)-3-nitrobenzoic acid has several applications in scientific research. It is used as a reagent in organic synthesis reactions to introduce a bromomethyl group into various compounds. This compound is also used as a fluorescent probe to study the binding interactions of proteins and nucleic acids. Additionally, it is used as a precursor for the synthesis of various bioactive molecules.
Method of Synthesizing Lenalidomide from 2-(Bromomethyl)-3-Nitrobenzoic Acid
A. N. Balaev, et al. Pharmaceutical Chemistry Journal, 2013, 46,676-678.
The synthesis steps of conventional lenalidomide are shown in Scheme 1, including four steps, with a yield of approximately 51%. An alternative preparation method (Scheme 2) greatly simplifies the synthesis of lenalidomide and enables it to be obtained in a higher yield (59.8%). The preparation procedure starting from 2-(Bromomethyl)-3-nitrobenzoic acid includes: · Condensation of 2-(Bromomethyl)-3-nitrobenzoic acid (III) with 3-aminopiperidine-2,6-dione (VI) at room temperature in DMF in the presence of NEt3 gave V. The yield of V under the selected reaction conditions was 86%. · Compound I was obtained by hydrogenation of V using palladium hydroxide. Use of palladium hydroxide instead of Pd on C enabled the reaction to be carried out at atmospheric pressure and the yield of the hydrogenation step to be increased to 79%. Thus, the overall yield of I for the whole scheme was 59.8%; the purity, 99.6% (by HPLC).
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