Practical Synthesis of 5-Aminolevulinic Acid from N-Acetylfurfurylamine

Kojiro SUZUKI*, Ken SASAKI and Yoshihiro MURAMOTO

Laboratory of Chemistry, Hiroshima-Denki Institute of Technology; 20-1,
Nakano, Aki-ku, Hiroshima-shi 739-0321 Japan
Department of Industrial Chemistry, Faculty of Engineering, Kinki University;
1-Umenobe, Takaya, Higashihiroshima-shi 739-2116 Japan

5-Aminolevulinic Acid (ALA) is known as a selective herbicide and one of the agricultural chemicals which promote the growth of plants. The authors studied on the practical synthesis of ALA from N-acetylfurfurylamine (AcFA). AcFA was converted to 2-acetamidomethyl-2,5-dimethoxy-2,5-dihydrofuran by electrolytic or bromine-methanol oxidation. It was changed to the tetrahydro compound by catalytic reduction with Raney Ni under ordinary temperature and pressure. The tetrahydro compound was oxidized to N-acetyl-ALA with potassium permanganate in a diluted sulfuric acid solution. N-Acetyl-ALA gave ALA hydrochloride by the hydrolysis with diluted hydrochloric acid. Overall yield of ALA hydrochroride was about 42%.

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