A kind of preparation method of ultrasonic-assisted n-(quinolin-2-yl) alkyl amides

An ultrasonic-assisted, alkyl amide technology, applied in organic chemistry, etc., can solve problems such as increased reaction costs, environmental side effects, harsh reaction conditions, etc., and achieve the effects of improved synthesis efficiency, simple reaction conditions, and easy-to-source sources

Inactive Publication Date: 2020-05-05
CENT SOUTH UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0009] Method 3) The source of raw material quinoline nitrogen oxide is easy to get, but the reaction conditions of this type of reaction are harsh, not only need to use volatile and toxic methylene chloride as the reaction medium, but also need to use oxalyl chloride or trifluorosulfonic anhydride and 2-fluoro Pyridine is used as an auxiliary agent, which not only increases the reaction cost, but also causes environmental side effects

Method used

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  • A kind of preparation method of ultrasonic-assisted n-(quinolin-2-yl) alkyl amides
  • A kind of preparation method of ultrasonic-assisted n-(quinolin-2-yl) alkyl amides
  • A kind of preparation method of ultrasonic-assisted n-(quinolin-2-yl) alkyl amides

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Effect test

Embodiment 1

[0066] Preparation of N-(quinolin-2-yl)acetamide:

[0067] In the 15mL round bottom flask, add quinoline nitrogen oxide 1.45g (10mmol) successively, acetonitrile 2.2mL (2.16g, 50mmol), the 732 cation exchange resins of 5% mass fraction, the ultrasonic reaction device of gained mixture is in 30W / 40KHz Medium ultrasonic reaction for 30 minutes. The resin catalyst in the reaction system was recovered by filtration, the unreacted acetonitrile in the reaction system was recovered under reduced pressure, and 1.72 g of the corresponding acetamide was obtained by recrystallization, with a yield of 93%.

Embodiment 2

[0075] Use 15W ultrasonic power instead of 30W ultrasonic power to assist the reaction:

[0076] In a 15mL round-bottomed flask, add quinoline nitrogen oxide 1.45g (10mmol) successively, acetonitrile 2.2mL (2.16g, 50mmol), the 732 cation exchange resins of 5% mass fraction, the ultrasonic reaction device of gained mixture at 15W / 40KHz Medium ultrasonic reaction for 60 minutes. Thin-layer chromatographic analysis confirmed that part of the quinoline raw material had not reacted completely. The resin catalyst in the reaction system was recovered by filtration, and the yield of N-(quinolin-2-yl)acetamide was calculated to be 68% by the liquid chromatography area normalization method.

Embodiment 3

[0078] Use 60W ultrasonic power instead of 30W ultrasonic power to assist the reaction:

[0079] In the 15mL round bottom flask, add quinoline nitrogen oxide 1.45g (10mmol) successively, acetonitrile 2.2mL (2.16g, 50mmol), the 732 cation exchange resins of 5% mass fraction, the ultrasonic reaction device of gained mixture is in 60W / 40KHz Medium ultrasonic reaction for 30 minutes. The resin catalyst in the reaction system was recovered by filtration, the unreacted acetonitrile in the reaction system was recovered under reduced pressure, and 1.72 g of the corresponding acetamide was obtained by recrystallization, with a yield of 93%.

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Abstract

The invention discloses an ultrasound-assisted preparation method of N-(quinoline-2-yl) alkyl amide. Under ultrasound assistance and catalysis of sulfonic acid cationic exchange resin, C2-N-amidationis performed on quinolone N-oxide, so as to obtain N-(quinoline-2-yl) alkyl amide. The method uses raw materials easy to obtain, is performed under simple, mild reaction conditions, is environmentallyfriendly and energy-saving, and has high reaction selectivity and yield; substrate functional groups are highly compatible; particularly, the sulfonic acid cationic exchange resin is used as an acidcatalyst, is easy to recycle and reuse, lowers reaction costs, and solves the pollution problem of traditional proton acid catalysis reaction, thereby having higher application value.

Description

technical field [0001] The present invention relates to a kind of preparation method of N-(quinolin-2-yl) alkyl amide, particularly relate to a kind of ultrasonic assisted amidation reaction of quinoline nitrogen oxide to synthesize N-(quinolin-2-yl) alkyl amide The compound method belongs to the technical field of organic intermediate synthesis. Background technique [0002] N-(quinolin-2-yl)alkylamides are a very important class of quinoline derivatives with various pharmacological activities, such as antibacterial activity (J.Med.Chem., 2017, 60, 9, 3755-3775 ); Antitumor activity (Nat.Chem., 2017, 9, 1110-1117); Antiallergic (J.Med.Chem., 1988, 31, 6, 1098-1115.) Trinucleotide repeat extension mutation inhibition Agents (Bioorg.Med.Chem.Lett., 2016, 26, 15, 3761-3764, J.Am.Chem.Soc.2005, 127, 12657-12665), etc.; [0003] The synthetic method of N-(quinolin-2-yl) alkylamide usually adopts the method of oxidizing quinoline compound at present, and main method is by follo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38C07D215/48C07D221/10
CPCC07D215/38C07D215/48C07D221/10
Inventor 肖芳肖元元曾明李娜殷丽蓉
Owner CENT SOUTH UNIV
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