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Synthetic method for isatoic anhydride derivative

A technology for the synthesis of isatoic anhydride and its synthesis method, which is applied in the field of synthesis of isatoic anhydride derivatives, can solve the problems of harsh reaction conditions, high cost, and reduced yield, and achieve mild reaction conditions, low production cost, and high synthesis yield Effect

Inactive Publication Date: 2013-01-09
NORTHWEST UNIV(CN)
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction has high requirements on temperature, time, and pH value, and the yield drops sharply when the optimal conditions are deviated from.
It can be seen that the traditional synthesis method of isatoic anhydride compounds has the disadvantages of harsh reaction conditions, high toxicity of reaction raw materials, high cost, serious environmental pollution, strong corrosion to equipment, and low reaction yield (Brouillette, Y.; Martinez, J .; Lisowski, V. Eur. J. Org. Chem.2009, 3487)

Method used

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  • Synthetic method for isatoic anhydride derivative
  • Synthetic method for isatoic anhydride derivative
  • Synthetic method for isatoic anhydride derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: prepare N-methylisatoic anhydride by N-methylaniline

[0027]

[0028] Add N-methylaniline (0.54 g, 0.005 mol), copper acetate (0.36 g, 0.002 mol), potassium iodide (0.17 g, 0.001 mol), palladium acetate (0.056 g, 0.00025 mol, 5 mol) into a 100 mL round bottom flask %) and 50 mL of acetonitrile, heated to 60°C in a mixture of carbon monoxide and oxygen at a ratio of 5:1 at an atmospheric pressure, detected the reaction by thin-layer chromatography, and cooled to room temperature after 11 hours, and the reaction mixture was decomposed with a short silica gel column The inorganic salt in the reaction was filtered off, the filtrate was spin-dried in vacuum, and the crude product of the reactant was recrystallized or separated by column chromatography to obtain 0.60 g of the pure product, which was a yellow solid with a yield of 68%.

[0029] Structural analysis: 1 H NMR (DMSO- d 6 , 400 MHz): δ = 7.97 (d, J = 6.8 Hz, 1 H), 7.85-7.82 (t, J = 6.8 Hz, ...

Embodiment 2

[0030] Embodiment 2: Similar to Embodiment 1, the difference is that potassium iodide is not added, and the reaction yield is only 40%.

Embodiment 3

[0031] Example 3: Preparation of 3,4-dimethyl-N-methylisatoic anhydride from 3,4-dimethyl-N-methylaniline

[0032]

[0033] Add 3,4-dimethyl-N-methylaniline (27.0 mg, 0.2 mmol), copper acetate (80.0 mg, 0.44 mol), potassium iodide (6.6 mg, 0.04 mmol) and palladium acetate ( 2.2 mg, 0..01 mmol) and 2 mL of acetonitrile, reacted at room temperature in carbon monoxide at an atmospheric pressure, detected the reaction by thin-layer chromatography until the reaction was completed, extracted the reaction mixture with water and ethyl acetate, combined the organic phases and vacuumed After spinning to dryness, the crude product of the reactant was separated by column chromatography to obtain 27.5 mg of the pure product, the product was a yellow solid, and the yield was 67%.

[0034] Structural analysis: 1 H NMR (DMSO- d 6 , 400 MHz): δ = 7.66 (s, 1 H), 7.20 (s, 1 H), 3.39 (s, 3 H), 2.33 (s, 3 H), 2.22 (s, 3 H); 13 C NMR (DMSO- d 6 , 100 MHz): δ = 158.8, 147.9, 147.7, 140.3, 1...

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PUM

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Abstract

The invention discloses a synthetic method for an isatoic anhydride derivative. The method includes: reacting polyaniline derivatives shown by a formula (II) or (III) with carbon oxide with existence of Pd and Cu, or Fe and Cu metal salt catalysts in catalytic amount to obtain the isatoic anhydride derivative shown by a formula (I), wherein R1 refers to hydrogen, halogen, nitryl, alkyl, alkoxy, ester, acyl, naphthenic base, aryl or arylalkyl, and the R2 refers to hydrogen, alkyl, alkoxy, naphthenic base, aryl or arylalkyl. The synthetic method for the isatoic anhydride derivative has the advantages of mild reaction condition, simplicity in operation, wide applicable range, low production cost, high synthetic yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of isatoic anhydride derivatives, belonging to the technical field of organic synthesis. Background technique [0002] Isatoic anhydride (Isatoic Anhydride) is a very useful chemical intermediate, it and its derivatives are widely used in the synthesis of agricultural chemicals, dyes, pigments, spices, essences, medicines, UV absorbers, foaming agents, barrier Combustibles, preservatives, bleaches, bactericides and sanitizers and other fine chemical products, and are also widely used in the field of tRNA and mRNA fluorescent labeling. [0003] At present, there are several methods for synthesizing isatoic anhydride derivatives: 1. Reaction of anthranilic acid derivatives with highly toxic chloroformate or triphosgene. 2. Oxidation of isatin derivatives: usually chromium trioxide or organic peroxyacids (such as peracetic acid, m-chloroperoxybenzoic acid) can be used to oxidize isatin derivatives to isatoic an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/26
Inventor 关正辉陈明任智卉
Owner NORTHWEST UNIV(CN)
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