Synthesis
(1) 3-Chloro-N-(3-hydroxyphenyl)propionamide
Dissolve 20 mmol of m-aminophenol in dichloromethane, add 20 mmol of triethylamine dropwise, and add 22 mmol of 3-chloropropionyl chloride dropwise while stirring at room temperature. After the addition is complete, stir at room temperature for 10 h. Wash three times with deionized water, and separate the organic phase by column chromatography to obtain 68% 3-chloro-N-(3-hydroxyphenyl)propionamide. (2) 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone
10 mmol of 3-chloro-N-(3-hydroxyphenyl)propionamide, 40 mmol of aluminum trichloride, and 6 mmol of N,N-dimethylacetamide were placed in a three-necked flask and reacted at 150 °C for 5 hours. 20 mL of ice water was slowly added dropwise to cool the mixture. The mixture was then heated to 90 °C and stirred for 1 hour. After cooling to room temperature, the mixture was filtered to obtain a red solid. Column chromatography yielded 88% 3,4-dihydro-7-hydroxy-2(1H)-quinolinone.
Description
3,4-Dihydro-7-hydroxy-2 (1H)-quinolinone is a useful organic and pharmaceutical intermediate. It can be used as the precursor of aripiprazole1, which is an antipsychotic medication. It is also an antitumor agent and hydroxyindole analog inhibitor tyrosinase melanoma.
Uses
3,4-Dihydro-7-hydroxyquinoline-2(1H)-one (Aripiprazole EP Impurity A) is an antitumor agent. Hydroxyindole analog inhibitor tyrosinase melanoma. This compound is also used in the preparation of aripiprazole (A771000).
