Synthetic method for 3,4-dihydro-7-hydroxy-2(1H)-quinolinone
A technology of dihydrogen and hydroxyl, which is applied in the direction of organic chemistry, can solve the problems of serious pollution, inconvenient operation, high temperature, etc., and achieve the effect of increasing yield, avoiding reaction temperature, and reducing reaction operation steps
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Embodiment 1
[0023] Embodiment one: the synthesis of (3-hydroxyphenyl)-3-chloropropionate
[0024] 100 mL of dichloromethane was added to a 250 mL three-neck flask, and 11.0 g (100.0 mmol) of resorcinol and 11.1 g (109.7 mmol) of triethylamine were sequentially added under stirring conditions. Stir and cool down to 0°C, slowly add 50 mL of dichloromethane dissolved with 12.7 g (100.0 mmol) of trichloropropionyl chloride dropwise, and after the dropwise addition, naturally raise the temperature to room temperature for 2 hours. Remove the insolubles by suction filtration, wash the filtrate with 5% hydrochloric acid, 5% sodium hydroxide, and water successively, separate the dichloromethane phase, dry it over anhydrous sodium sulfate, distill under reduced pressure to remove the solvent 18.7g of light yellow oil , yield 93.0%.
Embodiment 2
[0025] Example 2: Synthesis of 7-hydroxychroman-2-one
[0026] Add 18.7g (93.2mmol) of the reaction product (3-hydroxybenzene)-3-chloropropionate in the previous step into a 250mL three-necked flask, add 160mL of dichloromethane, lower the temperature to 0°C while stirring, and slowly add anhydrous tris Aluminum chloride 25.0 g (187.5 mmol), heat preservation and stirring for 1 hour. The temperature was raised to 40° C., and the reaction was refluxed for 24 hours. After the reaction, the temperature was lowered to -5°C, the methylene chloride was removed by pouring, and the ice-water mixture was slowly added dropwise to the remaining viscous solid, keeping the temperature below 10°C during the dropwise addition. After the dropping, stirred at 0-10°C for 3 hours, a large amount of solids precipitated out, filtered with suction, and dried in vacuo to obtain 13.0 g of yellow solids with a yield of 85.0%.
Embodiment 3
[0027] Example 3: Synthesis of 7-hydroxyl-3,4-dihydro-2(1H)-quinolinone
[0028] Dissolve 13.0g (79.2mmol) of 7-hydroxychroman-2-one, the reaction product of the previous step, into 130mL of methanol, add it to a 500mL autoclave, pass ammonia gas until the pressure is 0.5MPa, and raise the temperature to 80°C The reaction was stirred for 24 hours, and ammonia gas was supplemented during the reaction until the ammonia gas was no longer consumed. After the reaction was completed, the temperature was lowered to room temperature, and the pressure was released. The reaction solution was transferred to a 500 mL three-necked flask, 100 mL of water was added dropwise, and stirred for 3 hours, a large amount of light yellow solid precipitated. After suction filtration and drying, 11.2 g of a light yellow solid was obtained, with a yield of 87.0%.
[0029] As can be seen from the foregoing examples, the total yield of 7-hydroxychroman-2-one prepared by the method of the present inventi...
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