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ChemicalBook CAS DataBase List (E)-Methyl 1-acetyl-3-(Methoxy(phenyl)Methylene)-2-oxoindoline-6-carboxylate
1168152-07-5

(E)-Methyl 1-acetyl-3-(Methoxy(phenyl)Methylene)-2-oxoindoline-6-carboxylate synthesis

2synthesis methods
676326-36-6 Synthesis
Methyl 1-acetyl-2-oxoindoline-6-carboxylate

676326-36-6
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707-07-3 Synthesis
Trimethyl orthobenzoate

707-07-3
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(E)-Methyl 1-acetyl-3-(Methoxy(phenyl)Methylene)-2-oxoindoline-6-carboxylate

1168152-07-5
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Yield: 88.3%

Reaction Conditions:

with acetic anhydride in toluene at 120 - 130; for 6 h;Large scale;Temperature;

Steps:

1.2; 2.2; 3.2 (2) Synthesis of methyl 1-acetyl-3-(methoxyphenylmethylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylate
Add 18.9L of toluene into a 50L reactor, add 7.3L of acetic anhydride, and add 4kg of methyl 1-acetyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylate under stirring, the temperature was raised to 120-130°C, 9.4L (trimethoxymethyl)benzene was added dropwise, and the reaction was stirred for 6h. After the dripping starts, the internal temperature begins to decrease and is lower than 100°C, turn off the condensing reflux switch, distill out the low boiling point solvent, and control the temperature at 120-130°C, after 4 hours of reaction, there is precipitation, continue the reaction for 2 hours, stop heating, reduce to 0-10°C , continue to stir for 2 hours, after suction filtration, the filter cake was washed with 8.6L of toluene, then washed with a mixed solvent of 4.3L of toluene and 4.3L of ethyl acetate, and dried. The product obtained is 4.66 kg, with a yield of 88.3% and a purity of 92.11%.

References:

Chifeng Jingfang Pharmaceutical Development Co., Ltd.;Zhang Lihua;Wang Dongmei;Zhang Xiaoran;Meng Qingbin;Sheng Li CN111848486, 2020, A Location in patent:Paragraph 0024; 0040; 0043-0044; 0049; 0052-0053; 0058-0062