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CAS No. : | 86-48-6 | MDL No. : | MFCD00003960 |
Formula : | C11H8O3 | Boiling Point : | No data available |
Linear Structure Formula : | C10H6(COOH)(OH) | InChI Key : | SJJCQDRGABAVBB-UHFFFAOYSA-N |
M.W : | 188.18 | Pubchem ID : | 6844 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | In acetone; at 30℃; for 0.666667h; | 150 g <strong>[89365-50-4]salmeterol</strong> base and 1500 ml acetone were added to a 3 L flask,Warmed to 30 C stirring and dissolved, adding 68g 1-hydroxy-2-naphthoic acid,Stirring for 40 minutes precipitated a white solid, cooled to 5 C, crystallization insulation 3 hours,Suction filtered, washed and dried in vacuo to give <strong>[89365-50-4]salmeterol</strong> xinafoate in 94.1% yield. |
69% | In acetone; at 25 - 45℃; for 1.5h; | Example-8: Preparation of <strong>[89365-50-4]Salmeterol</strong> Xinafoate [I]100 g <strong>[89365-50-4]Salmeterol</strong> Base and 400 mL acetone were taken in round bottom flask at 25C. 47.54 g of Xinafoic acid was added and heated to get clear solution at 45C. The reaction mixture was stirred for 30 min and cooled to 25C. After stirring for 1 hour, 700 mL of methyltertbutyl ether was added and reaction mixture was further cooled to 10C and stirred for 2 hours. The product was filtered and washed with 150 mL chilled acetone. The product was dried in vacuum tray dryer for 12 hours at 45C to obtain 100 g (69%) of <strong>[89365-50-4]Salmeterol</strong> Xinafoate (I) with purity greater than 97% by HPLC. |
In diethyl ether; at 20℃; for 16h; | Step 11 N-(2-Hydroxy-2-(4-hydroxy-3-(hydroxymethyl)phenyl)ethyl)-6-(4-phenylbutoxy)hexan-1-aminium 1-hydroxy-2-naphthoate: Acetic acid (5 mL) and water (1 mL) was added to 1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-(6-(4-phenylbutoxy)hexylamino)ethanol (60 mg; 0. 13 mmol; 1. 00 equiv). The solution was stirred at about 70 C. for about 3 hours, and then concentrated in vacuo. The resulting residue was dissolved with water (40 mL), washed with ethyl acetate (20 mL) and ether (20 mL), and then the pH of the aqueous layer was adjusted to 8 with a saturated sodium bicarbonate solution. Following standard extractive workup with ethyl acetate, the crude residue was dissolved in diethyl ether (10 mL). 1-hydroxy-2-naphthoic acid (50 mg; 0.27 mmol; 2.12 equiv) was added and the mixture was stirred at ambient temperature for about 16 hours. The solid was collected by filtration and washed with diethyl ether to give the title compound as white solid (30 mg; 39% yield). 1H NMR (300 MHz, DMSO) delta: 9.43 (s, 1H), 8.49 (s, 2H), 8.20 (d, J=7.8 Hz, 1H), 7.70 (m, 2H), 7.44 (t, J=7.2, 7.8 Hz, 1H), 7.38~7.25 (m, 4H), 7.17 (m, 3H), 7.07 (d, J=8.1 Hz, 1H), 6.96 (s, d, J=8.4 Hz, 1H), 6.77 (d, J=8.1 Hz, 1H), 6.00 (s, 1H), 5.03 (t, J=4.8, 4.8 Hz, 1H), 4.78 (d, J=9.0 Hz, 1H), 4.49 (d, J=4.5 Hz, 2H), 3.34 (m, 4H), 3.07~2.90 (m, 4H), 2.58 (t, J=6.9, 7.8 Hz, 2H), 1.63~1.50 (m, 8H), 1.33 (m, 4H). LC-MS: m/z=416 (MH)+. |
20.75 g | Mixture of <strong>[89365-50-4]Salmeterol</strong> base (30 grams) and methanol (150 mL) were taken in round bottom flaskand stirred for clear solution at 25-30 C. Activated carbon (3.0 grams) was added and stirred for30 minutes at 25-30 C. Filtered the reaction mixture through hyflo bed and washed with methanol(30 mL). 1-hydroxy-2-napthoic acid (13.59 grams) was added to the filtrate at 30±2 C. Stirred the reaction mixture for 1.0 hour at 30±2 C and cooled to 18-22 C. Stirred the reaction mixture for 2.0 hours and the product was filtered, slurry washed with chilled methanol (60 mL). Dried the product in vacuum tray dryer for 12 hours at 40-45 C to obtain of <strong>[89365-50-4]Salmeterol</strong> Xinafoate (36 grams).; Mixture of?<strong>[89365-50-4]Salmeterol</strong> Xinafoate (25 grams) and methanol (150 mL) were taken in round bottom flask and heated at 45-50 C to get clear solution. Activated carbon (NoritDarco G60) (1.25 grams) was added and stirred for 15 minutes at 45-50 C. Filtered the reaction mixture was through hyflowbed and washed with methanol (8.33 mL). The filtrate was taken into round bottom flask and heated at 45-50 C to get clear solution. Cooled the reaction mixture slowly to 20±2 C and stirred for 4.0 hours. Filtered the precipitated product and slurry washed with chilled methanol (25 mL). Dried the product in vacuum tray dryer for 12 hours at 40-45 C to obtain pure <strong>[89365-50-4]Salmeterol</strong> Xinafoate (20.75 grans).1HNMR (DMSO, 300 MHz): 1.29-1.64 (m, 121-1), 2.50-2.58 (m, 2H), 2.91-3.10 (m 4H), 127-3.34(rn, 4H), 4.5 (s 2H), 4.83-4.87 (d 2H), 5.05 (br s 1H), 6.13 (br s IH), 6.77-6.79 (d IH), 7.02-7.08(rn 2H), 7.13-7.18 (m 3K), 7.23-7.28 (m 3K), 7.36-7.40 (m 21-1), 7.43-7.48(m 1H), 7.70-7.79 (m2H), 8.19-8.22 (d 1K), 8.82 (br s IH), 9.52 (br s 1K).MS: m/z = 416 [M+Hj. |