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Preparation method of nabumetone intermediate 2-methoxyl-6-naphthaldehyde

A technology of nabumetone and methoxynaphthalene, which is applied in the field of biomedicine, can solve the problems of poor selectivity and high price, and achieve the effects of low cost, high yield and mild reaction conditions

Inactive Publication Date: 2015-03-18
FUJIAN LIFEIKE BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of this invention is to provide a kind of preparation method of nabumetone intermediate 6-methoxy-2-naphthaldehyde, so as to overcome defects such as high price and poor selectivity in the prior art

Method used

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  • Preparation method of nabumetone intermediate 2-methoxyl-6-naphthaldehyde
  • Preparation method of nabumetone intermediate 2-methoxyl-6-naphthaldehyde

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Embodiment 1

[0020] Preparation of 6-bromo-2-methoxynaphthalene

[0021] In a 1 L reactor, add 8 g of 2-methoxynaphthalene, 24 g of bromine, 24 g of zinc-copper alloy (the content of zinc in the zinc-copper alloy is 50%) and 50 mL of 50% acetic acid aqueous solution Medium, 80 o C for 15 hours. After filtration, 200 mL of water was added to the filtrate, suction filtered, and dried to obtain 10.1 g of 6-bromo-2-methoxynaphthalene with a purity of 98.91% and a yield of 88%. figure 1 It is the nuclear magnetic spectrum of the 6-bromo-2-methoxynaphthalene of this embodiment 1, wherein, 1 H NMR (400 MHz, CDCl 3 ) δ 7.92 (d, J = 1.6 Hz, 1H), 7.62 (dd, J = 15.8, 8.9 Hz, 2H), 7.50 (dd, J = 8.7, 1.9 Hz, 1H), 7.16 (dd, J = 9.0, 2.5 Hz, 1H), 7.10 (d, J = 2.3 Hz, 1H), 3.92 (s, 3H). figure 2 It is the infrared spectrogram of the 6-bromo-2-methoxynaphthalene of this embodiment 1.

[0022] Preparation of 2-methoxy-6-naphthaldehyde

[0023] In a 1L reaction kettle, add 200 mL of anhy...

Embodiment 2

[0025] Preparation of 6-bromo-2-methoxynaphthalene

[0026] Add 8 g of 2-methoxynaphthalene, 24 g of bromine, 19.2 g of zinc-copper alloy (the zinc content in the zinc-copper alloy is 75%) and 15 mL of 50% acetic acid aqueous solution in a 1 L reactor ,80 o C for 6 hours. After filtration, 100 mL of water was added to the filtrate, suction filtered, and dried to obtain 9.5 g of 6-bromo-2-methoxynaphthalene with a purity of 96.5% and a yield of 82.5%.

[0027] image 3 It is the high performance liquid chromatogram of the 6-bromo-2-methoxynaphthalene of this embodiment 2. The sample was analyzed by Shimadzu LC-20AD, and the peak time of 6-bromo-2-methoxynaphthalene was detected to be 8.015 minutes. The normalization process was performed according to the peak area of ​​each peak in the original spectrum, and the sample purity was 97.39%.

[0028] Then according to the steps described in Example 1, the nabumetone intermediate 2-methoxy-6-naphthaldehyde was prepared, with ...

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Abstract

The invention discloses a preparation method of a nabumetone intermediate 2-methoxyl-6-naphthaldehyde. The preparation method comprises following steps: with 2-methoxylnaphthalene as an initial raw material, performing bromination to obtain 1,6-dibromo-2-methoxylnaphthalene; performing metal reduction to prepare 6-bromo-2-methoxylnaphthalene with a zinc-copper alloy as a reducing agent in a solvent, wherein a mass fraction of zinc is 50-100%; and further carrying out a Grignard reaction to prepare the 2-methoxyl-6-naphthaldehyde. The method is low in cost, is mild in reaction conditions and is good in selectivity.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to a method for synthesizing a nabumetone intermediate 2-methoxy-6-naphthaldehyde. Background technique [0002] Nabumetone (Nabumetone), also known as Napromone, Rilipene, and Nabumetone, has a chemical name of 4-(6-methoxy-2-naphthyl)-2-butanone, which was developed by the British Beecham Company A new generation of non-steroidal anti-inflammatory analgesics, first sold in Ireland under the trade name RELIFEX in 1985. Nabumetone belongs to the prodrug of ketone structure, which has antipyretic, analgesic and anti-inflammatory effects, and it can be metabolized into biologically active 6-methoxy-2-naphthaleneacetic acid (6-MAN ), metabolites have no enterohepatic circulation, but are excreted through urine. Nabumetone is a non-acid anti-inflammatory drug, which has no direct stimulating effect on the gastrointestinal mucosa. It is well tolerated after long-term use and has a long half-...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/28
CPCC07C45/455C07C41/22C07C41/24C07C47/575C07C43/225
Inventor 吴祥黄微
Owner FUJIAN LIFEIKE BIOTECH
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