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Method for synthesizing 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine

A synthesis method and tetramethyl technology are applied in the synthesis field of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine, which can solve the problem of high pollution and safety It has the problems of poor performance and high cost, and achieves the effects of high reaction yield, high safety and simple operation.

Active Publication Date: 2012-12-05
重庆莱美隆宇药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine is reported in this document by 2,6-dichlorohexane and benzene through ring 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalene is prepared by combining, and then nitrated, and then catalytic hydrogenation reduction is obtained. The total yield of the three steps is only about 15%, especially It is the following two steps, and the yield of each step is only 20%. In these three steps, benzene with high toxicity is used for cyclization, which causes great pollution in the nitration process, high cost of catalytic hydrogenation, poor safety, environmental protection, and high cost. Not suitable for industrial production

Method used

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  • Method for synthesizing 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine

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Embodiment 1

[0014] 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenecarboxamide, its structural formula is as follows:

[0015]

[0016] Take 20g into a three-necked flask, add 200ml of ethylene glycol and 5.8g of potassium hydroxide, raise the temperature to 100°C, stir for 2 hours, cool down, pour the reaction solution into a large amount of water, leave it overnight, filter, and recrystallize the solid with methanol / water , to obtain yellow solid 14.2g, yield 85.7%, mp: 71-74, 1H-NMR (300MZ, CHCl3) 1.24 (6H) 1.27 (6H) 1.69 (4H) 3.5-3.9 (2H) 6.56 (1H) 6.68 ( 1H) 7.13(1H).

[0017] Wherein, the preparation method of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarboxamide can refer to the description in EP0478787.

Embodiment 2

[0019] Put 20g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarboxamide into a three-necked flask, add 200ml glycerol and 7.0g sodium hydroxide, and heat up to 150°C , stirred for 2 hours, cooled, the reaction solution was poured into a large amount of water, left overnight, filtered, and the solid was recrystallized from methanol / water to obtain 14.5 g of a yellow solid, with a yield of 87.5%.

Embodiment 3

[0021] Put 18g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarboxamide into a three-necked flask, add 100ml of 1,2-propanediol and 6.5g of sodium hydroxide, and heat up to 130°C, stirred for 2 hours, cooled, poured the reaction solution into a large amount of water, left overnight, filtered, and recrystallized the solid with methanol / water to obtain 12.1 g of a yellow solid, with a yield of 83.0%.

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Abstract

The invention discloses a synthesis method of 5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthylamine. The synthesis method comprises the following steps: the 5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthoamide reacts with sodium hydroxide in a high boiling point solvent; a protective group of the amino group is removed at temperature between 100 DEG C and 200 DEG C; a reaction solution is deposited with water and filtered; a solid product obtained is recrystallized to obtain the 5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthylamine. The method is environmentally friendly,has little pollution, low cost, simple operation, high safety, high reaction yield and high transformation rate reaching more than 80 percent and requires no adoption of expensive Pd-C catalysts and no catalytic hydrogenation. If necessary, the obtained 5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthylamine can be condensed and hydrolyzed to obtain tamibarotene.

Description

technical field [0001] The invention relates to a synthesis method of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine. Background technique [0002] 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine, structural formula is as follows formula (I), is the main raw material of synthetic tamibarotene (tamibarotene), he The molecular structural formula of mibarotene is shown in formula (II). [0003] [0004] Tamibarotene is a retinoic acid agonist, its preparation and efficacy are described in J.med.chem.1988, 31, 2182-2192. Tamibarotene has valuable pharmacological value and has been marketed as a therapeutic drug for acute promyelocytic leukemia in Japan. [0005] Also described in J.med.chem.1988,31,2182-2192 the synthetic method of tamibarotene, adopts 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl- 2-naphthylamine is prepared by condensing 2-naphthylamine with methyl p-formate benzoyl chloride, followed by hydrolysis. The method has high yield and is suitable for i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/58C07C209/62
CPCY02P20/55
Inventor 彭建坤安林
Owner 重庆莱美隆宇药业有限公司
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