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Preparation method for 2,3,4-trimethoxy benzonitrile

A technology of trimethoxybenzonitrile and trimethoxybenzene, which is applied in the field of preparation of 2,3,4-trimethoxybenzonitrile, can solve the problems of high comprehensive cost and many reaction steps, and reduce production cost and steps Less, less expensive effects

Inactive Publication Date: 2013-12-18
HENAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a preparation method of 2,3,4-trimethoxybenzonitrile, which can prepare trimethoxybenzonitrile in one step, and overcome the problems of many reaction steps and high comprehensive cost in the existing method

Method used

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  • Preparation method for 2,3,4-trimethoxy benzonitrile
  • Preparation method for 2,3,4-trimethoxy benzonitrile
  • Preparation method for 2,3,4-trimethoxy benzonitrile

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Embodiment 1

[0028] Add 0.5mmol 1,2,3-trimethoxybenzene, 0.25mmol I 2 , 0.4mmol copper chloride, 0.4mmol silver nitrate, 0.25mmol potassium ferricyanide, 1.5mL 1-n-butyl-3-methylimidazolium tetrafluoroborate. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 180° C., and magnetically stirred at 180° C. for 35 hours. After the reaction was completed, the reaction system was cooled to room temperature. The reacted mixture was purified by column chromatography. The obtained 2,3,4-trimethoxybenzonitrile product was a white solid with a yield of 72%. use 1 H-NMR and 13 C-NMR confirmed the structure of the product, which 1 H-NMR diagram and 13 C-NMR charts are shown in figure 1 and 2 . 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) = 7.28 (d, J = 8.0 Hz, 1H), 6.70 (d, J = 8.0 Hz, 1H), 4.06 (s, 3H), 3.92 (s, 3H), 3.87 (s, 3H). 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) = 158.1, 155.9, 141.9, 128.9, 116.7, 107.6, 99.1, 61.8, 61.1, 56.4.

Embodiment 2

[0030] Add 2.5mmol 1,2,3-trimethoxybenzene, 1.25mmol I 2 , 2mmol copper chloride, 2mmol silver nitrate, 1.25mmol potassium ferricyanide, 10mL 1-n-butyl-3-methylimidazolium tetrafluorophosphate. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 190° C., and magnetically stirred at 190° C. for 20 hours. After the reaction was completed, the reaction system was cooled to room temperature. The reacted mixture was purified by column chromatography. The obtained 2,3,4-trimethoxybenzonitrile product was a white solid with a yield of 53%. use 1 H-NMR and 13 C-NMR confirms the structure of product, and its spectrogram data is identical with embodiment 1.

Embodiment 3

[0032] Add 1 mmol 1,2,3-trimethoxybenzene, 0.5 mmol I 2 , 0.8mmol copper chloride, 0.8mmol silver nitrate, 0.5mmol potassium ferricyanide, 3mL 1-n-hexyl-3-methylimidazolium tetrafluoroborate. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 185°C, and magnetically stirred at 185°C for 25 hours. After the reaction was completed, the reaction system was cooled to room temperature. The reacted mixture was purified by column chromatography. The obtained 2,3,4-trimethoxybenzonitrile product was a white solid with a yield of 42%.

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Abstract

The invention belongs to the technical field of chemical intermediate preparation, and particularly relates to a preparation method for 2,3,4-trimethoxy benzonitrile. The preparation method comprises the steps of dissolving 2,3,4-trimethoxy benzene, a cyanide, a catalyst, I2 and copper salt in ionic liquid, and carrying out reaction for over 5 hours to obtain 2,3,4-trimethoxy benzonitril under the condition of temperature controlled to be 160-240 DEG C and an enclosed condition. The raw material 2,3,4-trimethoxy benzene adopted in the invention is cheap, the steps of overall synthetic route are less and the operation is simple, therefore the production cost is decreased effectively.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical intermediates, in particular to a preparation method of 2,3,4-trimethoxybenzonitrile. Background technique [0002] 2,3,4-trimethoxybenzonitrile is a relatively expensive pharmaceutical intermediate (Journal of Medicinal Chemistry, 2009, 52(7):1873-1884), for example, it can be used to synthesize 2,3,4-trimethoxy base benzoic acid, and further synthesize 5,6,7-trialkoxy-N-aryl-4-aminoquinazoline derivatives with therapeutic properties for malignant tumors, for the synthesis of analgesic, coronary artery vasodilator, anti- 2,3,4-Trimethoxybenzoic acid-1-piperazinylethyl ester with convulsive and hypotensive effects (Rakhit S, Bagli J F. 2-(Piperazinyl)-4-pyrimioinamines[P]. US 4333937. 1982 ). At present, the preparation method of trimethoxybenzonitrile is mainly as follows: (1) Preparation with trimethoxybenzoic acid as raw material. For example, trimethoxybenzoyl chloride is ge...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/54C07C253/14
Inventor 任运来田欣哲李国芝巫滨牛睿祺侯超东
Owner HENAN UNIV OF SCI & TECH
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