Method for producing (3-hydroxypropyl)naphthols

FIELD: chemistry.

SUBSTANCE: invention refers to a method for the one-stage production of (3-hydroxypropyl)naphthols of having a structure of R1=CH2CH2CH2OH, R2=OH, R3=H; R1=OH, R2=CH2CH2CH2OH, R3=H; R1=OH, R2=CH2CH2CH2OH, R3=CH2CH2CH2OH; R1=OH, R2=T-Bu, R3=CH2CH2CH2OH, effective biologically active substances of neutropic action. The method consists in conducting a reaction of α-, β-naphthols, their derivatives or their sodium salts with allyl alcohol and alkali at temperature 100-170°C. A purified product yield is 40-60%.

EFFECT: higher yield.

4 ex

 

The invention relates to the field of synthetic organic chemistry, more specifically to obtain (3-hydroxypropyl)-naphthols, structurally related to a class of phenylpropanoids - effective biologically active substances neurotropic action [V. A. Kurkin, A. V. Dobrosav, I. N. Titov, A. V. Valezuela, E. S. Petrova, N. In. Zhestkov, I. Yu. Klimov. // Plant resources, 2003, vol. 3. C. 115-121]. 1-(3-Hydroxypropyl)-2-naphthol(1) and 2-(3-hydroxypropyl)-1-naphthol (2) is proposed to obtain ionic liquids [Dong Jin Hong, Dong Wook Kim // Tetrahedron Letters 2010, 51, 54-56]. Based on the compound (2) synthesized a number of biologically active products with anti-cancer effect [Ngamhong Kongkathip, Suwaporn Luangkamin, Chak Sangma at all. // J. Med. Chem. 2004, 47, 4427-4438].

All known methods for the preparation of hydroxypropranolol multistage. The scheme of obtaining 1-(3-hydroxypropyl)-2-naphthol(1) from 2-naphthol in a total yield of 30% are presented below:

Ether (3), formed by boiling 2-naphthol with allylbromide in the presence of K2CO3, regroup 1-(allyl)-2-naphthol (4). Gladfeld J. W. E., Rietz, E. J. J. Am. Chem. Soc. 1940. V. 62. 974. Based on the compound (4) is obtained Boran-tetrahydrofuranyl complex, which is oxidized with hydrogen peroxide in alkaline medium, and from the products isolated compound 1 with an exit at this stage 75%. Tolbert L. M., L. C. Harvey, R. C. Lum // J. Phys. Chem. 1993. V. 97. 13335-133340.

On�t hese for the execution of the three-stage approach used to obtain compounds based on 2 naphthol-1 [Kongkathip N., Luangkamin S., Kongkathip B. Songma Ch., Grigg R., Kongsaere P., Samran P. N., Piyaviriyagyl S., Siripong P. Bioorganic & Medicinal Chemistry 2003. V. 11. N 14. P. 3179-3191].

A method of obtaining compound 1 by condensation of ester (3) with derivatization chromane (7), which is then reduced with preparation of the compound 1 [S. Marcinkiewicz, J. Green, P. Mamalis // Tetrahedron 1961. T. 14. C. 208-222] in the diagram:

Abeywickrema N. A., Beckwith, A. L. J., Gerba S / // J Org. Chem. 1987, 52, 4072-4078. The disadvantage of this method is a multistage process.

A method of producing the compound 1 with a yield of 46% by restoring splitomicin (8) in the scheme:

The disadvantage Posakony J., Hirao M., Sam S., Simon ja, Bedalov A. // J. Med. Chem. 2004, 47, 2635-2644 is the complexity of the synthesis of the starting splitomicin.

A great number of studies aimed at obtaining compounds 1 with the use of propionic acid derivative (9) in the scheme:

Ranade A. A., Joseph A. R., V. B. Kumbhar, M. Paradkar V. // J. Chem. Researh, Miniprint; nb. 11; (2003); p. 1175-1184. The main disadvantage of this method is the multistage and the use of metal hydrides as reducing agents.

The modern approach to obtaining hydroxypropranolol may be reduced in one stage using the known method of obtaining chromenes interaction naphthol-2 with proargi�new alcohol in the presence of ruteniysoderzhaschim catalyst. Kanao, Keiichiro; Miyake, Yoshihiro; Nishibayashi, Yoshiaki // Organometallics(2010), 29(9), 2126-2131. The chromenes, as we know, may be subjected to reduction with hydride to produce a compound 1.

This approach is hampered by the complexity of the synthesis and use ruteniysoderzhaschim catalyst.

Analysis of all the known methods of obtaining hydroxypropranolol indicates their one restrictive feature: in the process of synthesis hydroxiproline group is always formed in the ortho-position to the hydroxy-group naphthols. Another disadvantage of the known processes based on the availability of α and β-naphthol is multistage and the use of expensive reagents.

Proposed one-step method for producing hydroxypropranolol of naphthols is about the interaction of their alkali metal salts with allyl alcohol in the presence of excess alkali. The process can take place in the presence or absence of aromatic hydrocarbons toluene, or xylene. It can be carried out at atmospheric pressure or under pressure up to 10 atmospheres in an autoclave.

In carrying out the process at atmospheric pressure, advantageously in the presence of aromatic hydrocarbons (the most convenient to use are toluene or xylene), which provides for the removal from the reaction mass formed during the reaction water�. In the presence of alkali water reacts with allyl alcohol, which leads to the formation side of the most difficult to separate methylated products.

From hydrocarbons suitable for use is toluene or xylene.

Due to the high oxidation in air alkaline reaction mass, it is protected by a current of inert gas in the process of synthesis and neutralize it at the final stage of the reaction. Deviation from the specified parameters of the interaction of naphthols with allyl alcohol using a catalyst changes the nature of the formed products and leads to the preferential formation of allylalcohol [Das, Biswanath; Veeranjaneyulu, Boyapati; Krishnaiah, Maddeboina; Balasubramanyam, P. // Synthetic Communications(2009), 39(11), 1929-1935], esters [Gladfeld J. W. E., Rietz, E. J. J. Am. Chem. Soc. 1940. V. 62. 974], and cyclization products [Kimura, Masanari; Fukasaka, Miki; Tamaru, Yoshinao // Synthesis(2006), (21), 3611-3616].

Synthesis of 1-(3-hydroxypropyl)naphthol-2 (1) of naphthol-2 is one-step in accordance with the scheme:

This process can be carried out under a pressure of 10 ATM in an autoclave or at atmospheric pressure in the flask. The structure of compound 1 was proved by spectral methods and transforming it into a well-known compound 7.

More economical autoclave option, but it is limited by the availability of special equipment, operated under pressure. In this CL�tea reagents, indicated in the figure, is maintained in an inert atmosphere in an autoclave at 170°C for 15 hours. The obtained reaction mixture is neutralized and a mixture of products containing 85% of compound (1). Cleaning product 1 is carried out by distillation in vacuum.

The possibility of a single step of obtaining compound 1 at atmospheric pressure. This embodiment is carried out in boiling allyl alcohol the influence of the β-naphtalate sodium, previously prepared from naphthol and alkali removal from the reactor the reaction of water with the use of inert solvents. The reaction and neutralization of the reaction mass is held in a stream of inert gas because of its high propensity to oxidation.

Formed by side in the reaction process naphthoquinones are catalysts of oxidation of the reaction mixture in air, which requires removing them from the reaction mixture without delay. This is achieved by washing the reaction products of chloroform, in which hydroxypropylmethyl poorly soluble. At the same time simplifies the selection of the product from the reaction mass. The interaction of α-naphthol with allyl alcohol in an alkaline medium proceeds according to the scheme:

The process is carried out at atmospheric pressure in a stream of inert gas - argon. The sequence of the stages is as follows: from�achala in the reactor is prepared α-naptalam sodium with removal of the reaction water by means of boiling xylene, and then is introduced into the reactor allyl alcohol and the reaction is carried out at boiling of the reaction mass. Compound 2 isolated from the reaction mass with a yield of 40% in the process of vacuum distillation.

The excess allyl alcohol promotes the accumulation of compound (11) in the reaction products.

Example of introduction hydroxypropyl group in para-position to the hydroxyl group of the naphthol is the interaction of 2-tert-butylnitrone (12) with allyl alcohol to obtain 2-tert-butyl-4-hydroxypropranolol-1(13):

These stages are conducted in a single vessel: first preparing tert-butylnaphthalene sodium boiling compounds 12 and alkali in xylene distillation of water, then the salt is boiled in allyl alcohol to produce a compound 13 without appreciable formation of by-products.

The proposed method has the following advantages:

1. He single-stage and implemented from the available products.

2. In contrast to the known methods allows you to enter in one stage hydroxypropyl group not only in the ortho-, but in the para-position to the hydroxyl group of the naphthol.

3. The method allows to obtain Naftali containing in the structure two hydroxiproline group. The above ideas are confirmed by the following examples.

Example 1. The preparation of the compound (1) at a pressure of 10 ATM (�wroclawiu method)

In a steel rotating autoclave with a capacity of 50 ml was placed 10 g (0.069 mol) of 2-naphthol, 15 ml of allyl alcohol and 2.9 g (0.073 mol) of granulated caustic soda, powdered, replacing the air with inert gas and the contents are heated while rotating the autoclave for 15 hours at 170°C. Then the autoclave was cooled to room temperature, opened and the reaction mixture is optionally placed 7 ml of hydrochloric acid, 7 ml of water and 20 ml of ether. The autoclave was sealed and heated to 100°C within one hour and after cooling is opened, the ethereal solution washed with water and evaporated. Get 14.4 g of a crystalline mass containing according to the GLC 86% 1-(3-hydroxypropyl)-2-naphthol (1). After distillation under vacuum gave 6.7 g of the fraction with b. p .. 175-185°C / 3-5 mm Hg.CT., contains according to GC 97% of base material 1. The yield of 48%. So a MP 127-129°C. After crystallization from a mixture of ether - hexane, MP of 132-133°C (according to [1] T. a MP 132.5-133.5°C). M+ 202 (mass by spectrometry according).

Signals PMR solution of compound 1 in CD3OD: 2.02 m, CH2; 3.22 T., CH2Ar; 3.60 T. CH2OH; D. 7.14 1H; 7.32 T. 1N; 7.46 T. 1N; 7.77 D., 1H; 7.79 D., 1H; 7.88-7.91 m 1N CH2coincided with those described for the PMR spectrum of the compound (1), filmed in a solution of CD3CN. [J. Posakony, M. Hirao, S. Stevens, J. A. Simon, A. Bedalov // J. Med. Chem. 2004. V. 47. P. 2635-2644].

Additionally the identification of compound 1 spent turning �th in the known compound 7. To a solution of 0.5 g of 98% of compound 1 in 0.2 ml of DMF was added at room temperature with stirring 0.2 ml of SOCl2(a rough allocation of SO2). The reaction mixture stood at 80°C for 20 minutes, then added 2 ml of water and boiled for another 30 minutes. The product was extracted with ether and the solvent evaporated. Received 0.4 g of substance containing according to the GLC 90% of 2,3,4-trihydroxypropane(7). It is purified by thin-layer chromatography, a MP 40-42°C. According to literature data t a MP 40-42°C [N. A. Abeywickrema, A. L. J. Beckwith, S. Gerba // J. Org. Chem. 1987. V. 52. P. 4072-4078].

The PMR spectrum of compound 7 in CDCI3, δ: 2.15-2.30 (m, CH2), 3.10 (t, J=6.1 Hz, CH2), 4.3 (t, J=5.1 Hz, CH2), 7.0-7.9 (m, 6H, Ar-H).

Example 2. The preparation of the compound 1 at atmospheric pressure. In a flask with inert gas, a stirrer and a reflux condenser are placed 2.84 g (0.02 mol) of β-naphthol, 2 g (0.05 mol) of powdered NaOH and 15 ml of ortho-xylene. From the reactor during the heating and stirring was distilled off for 30 minutes, 12 ml of wet ortho-xylene, is then added to the reactor 2.5 ml of allyl alcohol and heated to reflux for 1 hour 30 minutes, add a serving of 1.5 ml of allyl alcohol and boil for another 30 minutes. The reaction mass is diluted with acidified water and extracted with methyl tert-butyl ether. The extract is separated, washed with water and evaporated. Get 3.7 g of the solid product contained�asego according to GC 80% of compound 1. After rinsing with warm chloroform receive 2.0 g of compound 1(yield 50%) with a MP 127-129°C.

Example 3. The formation of compounds 2 and 11 at atmospheric pressure

In a glass flask is placed 2.4 g of crushed powder NaOH, 15 ml of freshly distilled toluene and 1.4 g of naphthol-1. With stirring in a stream of inert gas for 1 hour from the reactor is distilled off 8 ml of wet toluene. Then added to the reactor 15 ml of allyl alcohol and in a stream of inert gas is continued for 2 hours to drive away slowly from the reactor a mixture of toluene and allyl alcohol. The reaction mixture is cooled, dissolved in methyl tert-butyl ether and the solution washed with dilute hydrochloric acid until neutral. After evaporation of the solvent produced 2.1 g of a viscous oil, containing according to the GLC 31% of the initial 1-naphthol, 62% of 2-(3-hydroxypropyl)-1-naphthol(2), and 17% of 2, 4-di-(3-hydroxypropyl)-1-naphthol (11). This oil was distilled under vacuum, collecting 1.0 g of the fraction with Kip T. 185°C/ 3 mm Hg.PT. The product was then purified by crystallization from hexane with the addition of methyl tert-butyl ether. Get 0.8 g of compound 2 (yield 40%) with a MP 84-86°C. According to literature data t a MP of 86-87°C [J. Am. Chem. Soc. 1940. V. 62. R. 3067-3069] Found: 202.1 M., m/z(%): 202(M+98), 184 (99), 156 (69), 128(100).

Compound 11 is isolated from the reaction mixture by thin-layer chromatography on silica gel. Eluent ethanol:chloroform in the ratio of 10:1. Etc�. 161-164°C. Found: m/z=260.1405(M+44), 216 (39), 197 (100), 171 (75), 141 (45) 115 (37), 73 (62). C16H20O3. Calculated: m/z=260.1407 (mass by spectrometry according). The PMR spectrum in CD3OD, δ: 1.84 m(-CH2-); 1.88 m. (-CH2-); 2.82 t. J=7.0 Hz (-CH2-); 3.10 t. J=7.0 Hz(-CH2-); 3.57 t. J=7.0 Hz (-CH2OH); 3.69 t. J=7.0 Hz (-CH2OH); 7.10 S. ArH; 7.3-7.4 m. 2H, 7.90-7.95 m. 1H, 8.15-8.22 m. 1H, ArH.

NMR spectrum of13C: C1225.61; C1528.13; C1132.27; C1433.42; C1360.38; C1661.00 C3121.20; 121.9; 123.07; 123.81; 123.43; 124.49; C5126.12; C4129.33; C10131.22; C1147.65.

Example 4. Receiving 2-tert-butyl-4-(3-hydroxypropyl)naphthol-1 (13)

In a flask with a stirrer, a reflux condenser and entering into the reaction mass with an inert gas (argon) was placed 1.2 g (0.006 mol) of 2-tert-butyl-1-naphthol, 1.5 g of crushed NaOH (0.038 mol) and 15 ml of toluene. The contents heated to boiling and within 30 minutes drive away 12 ml of wet toluene was then added 3.5 ml (0.06 mol) of allyl alcohol and the resulting solution was boiled for one hour.

To the reactor in one portion was added a solution of 5 ml of concentrated hydrochloric acid in 20 ml of water. Separates oil from which falls 0.65 g (yield 42%) of colorless crystals of compound 13. T. PL. 120-122.5°C (CHCI3).

Found: M-1257. 155. C17H22O2(gas chromatography / mass by spectrometry according). Calculated: M-1257. 154. UV spectrum in methanol: λmax242 and 302 nm; s of 25 nm.

The PMR spectrum in CD3OD: δ 1.43 S. 9H. C4H9-tert; 1.88 m. 2H. -CH2-; 2.98 t. J=7.5 Hz, 2H; 3.30 p. OH; 3.62 t. J=6.2 Hz, 2H. -CH2OH; 7.25 S. ArH; 7.34-7.36 m. 2H, 7.87 m. 1H, 8.02 m. 1H, ArH.

NMR spectrum of13From: C1228.97; C1529.98; C1133.61; C1434.27; C13121.02; C3121.02; 123.56; 124.81; 124.9; 125.33; C5127; C4129.12; C10130.3; C2130.92; C1147.64.

A method of producing in one stage (3-hydroxypropyl)naphthols of this structure by the reaction of α-, β-naphthols, their derivatives or their sodium salts with allyl alcohol and an alkali at a temperature of 100-170°C.



 

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