4-Aminoacetanilide Explained

4-Aminoacetanilide or paracetamin is a chemical compound which is a amino derivative of acetanilide and para-isomer of aminoacetanilide. There are two other isomers of aminoacetanilide, 2-aminoacetanilide and 3-aminoacetanilide. Aminoacetanilide derivatives are important synthetic intermediates in heterocyclic and aromatic synthesis. These derivatives have found applications in pharmaceutical industry and dyes and pigment industry.^[1]

Synthesis

Becillus cereus converts 4-phenylenediamine to 4-aminoacetanilide.^[2] Reduction of 4-nitroacetanilide by hydrogenation catalyst generates 4-aminoacetanilide.^[3] Green synthesis of p-Aminoacetanilide is achieved by reducing p-nitroaetanilide using Zn/NH₄Cl in water.^[4] Number of methods are available to reduce 4-nitroacetanilide using different catalyst and reaction conditions.

Uses

4-Aminoacetanilide is used as in intermediate in the production of some dyes. 4-aminoacetanilide is also used for the synthesis of beta-lactams.^[5]

Notes and References

1. Singh. Raman. Kau. Rajneesh. Singh. Kuldeep. 2016. A review on Synthesis of Aminoacetanilides. Journal of Integrated Science and Technology. 4. 111–120. 2321-4635. Google Scholar.
2. Mulyono. Takenaka. Shinji. Sasano. Yasuhiro. Murakami. Shuichiro. Aoki. Kenji. February 2007. Bacillus cereus strain 10-L-2 produces two arylamine N-acetyltransferases that transform 4-phenylenediamine into 4-aminoacetanilide. Journal of Bioscience and Bioengineering. en. 103. 2. 147–154. 10.1263/jbb.103.147. 17368397.
3. 李. 玉涵. 侯. 洁. 王. 越. 吕. 连海. 2009. 催化加氢制备对氨基乙酰苯胺. 染料与染色. 46. 2. 42–45. 1672-1179.
4. 曹. 玮. 曲. 波. 梁. 足培. 2004. 对氨基乙酰苯胺合成绿色工艺的研究. 化工时刊. 4. 55–56. 1002-154X.
5. Tahriri. Mozhgan. Yousefi. Mohammad. Mehrani. Kheirollah. Tabatabaee. Masoumeh. Ashkezari. Mahmood Dehghani. August 2017. Synthesis, Characterization and Antimicrobial Activity of Two Novel Sulfonamide Schiff Base Compounds. Pharmaceutical Chemistry Journal. 51. 5. 425–428. 10.1007/s11094-017-1626-z. 25837758. 0091-150X.