The pineal hormone melatonin is conveniently prepared in a simple one pot operation by treating 4-methoxyphenylhydrazine hydrochloride(6) with acetic anhydride and 4-aminobutyraldehyde dimethylacetal(4) in a mixed solvent system of acetic acid / ethanol / water.
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Hwangyy et al. (1999) studied this question.
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