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CAS No. : | 86-86-2 |
Formula : | C12H11NO |
M.W : | 185.22 |
SMILES Code : | C1=CC=CC2=CC=CC(=C12)CC(N)=O |
MDL No. : | MFCD00004047 |
InChI Key : | XFNJVKMNNVCYEK-UHFFFAOYSA-N |
Pubchem ID : | 6861 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
* 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 |
---|---|---|
72% | With ammonium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 0.166667h; | 1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was added to methylene chloride (0.8 mL)And a catalytic amount of DMF were added and while stirring,Further oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 eq.) Was added dropwise,Followed by stirring at room temperature for 15 minutes. After concentrating the resulting solution under vacuum,Was dissolved in tetrahydrofuran (0.8 mL).Ammonia water (28%, 450.4 mg, 7.50 mmol, 15.0 eq.) At 0 C. was added to the solution,It was then stirred at room temperature for 10 minutes. After concentrating the resulting solution under vacuum,Silica gel column chromatography (chloroform / methanol(10/1, Rf = 0.50)) to obtain the target substance (Y-015) as a white solid (yield 72%). |
With 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 0 - 20℃; | General procedure: To an over-dried 100 mL three-necked flask, the carboxylic acid (10 mmol), DMF (5 drops) and DCM (30 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol) was added dropwise at 0 C resulting in vigorous bubbling. The mixture was stirred for 3 h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride was used immediately without further purification. To a solution of the acid chloride in DCM (30 mL) ,a solution of 1,1,1,3,3,3-hexamethyldisilazane (30 mmol) in DCM (10 mL) was added dropwise at 0 C, and the solution was then allowed to warm to room temperature. After stirring overnight, the reaction system was quenched with 1 M HCl aq. and saturated aqueous NH4Cl (excess amount) and the organic layer was separated. The aqueous layer was extracted with DCM (2x15 mL). The combined organic layers were washed with saturated aqueous NH4Cl (30 mL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude material was purified by recrystallization from EtOAc and hexane. The resulting product (5 mmol), 8-bromomethylquinoline (6 mmol), Al2O3 (50 mmol), KOH (25 mmol) and dioxane (30 mL) were added to an over-dried 100 mL three-necked flask. The mixture was stirred for 8 h at 60 C and then was filtered through a celite pad. The filtrate was washed with H2O (30 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (2x15 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, filtrated and evaporated in vacuo. The resulting crude amide was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 1/1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Unless otherwise specified, carboxylic acid (0.542 mmol), TCT (0.0400 g, 0.216 mmol) and K2CO3 (0.2247 g, 1.626 mmol) were mixed together and hand ground for one minute using porcelain mortar and pestle. After addition of ammonium thiocyanate (0.0495 g, 0.650 mmol), the mixture was ground manually for further five minute. During the grinding, THF (calculated to be less than 1 L/mg of solids) was added to aid homogeneous mixing. The crude material was then purified by short column chromatography (column diameter 1.5 cm, packed with 3-4 g silica gel ) using 40-50% ethyl acetate/hexane as an eluent. | |
88% | To a solution of 2-(naphthalen-1-yl)acetic acid (1.50 g, 8.01 mmcl, 1.00 equiv.) in dry CH2C12 (10.0 mL, 0.801 H) was added thionyl chloride (6.73 mL, 92.6 rnmol, 11.5 equiv.) at 0 C, then the reaction was refluxed for 2 h. The solvent was evaporated and the residue wasazeotroped with toluene (2 xlO.0 mL) . To the crude acyl chloride was added THF (30.0 mL) and NHsH2O (30.0 mL) under vigorous stirring at 0 C. After the reaction mixture was stirred at room temperature for overnight, the solvent was removed. The residue was purified by column chromatography using with EtOAc:hexane (1 :2 (v/v)) to afford thetitle compound as a white solid (1.31 g, 7.07 mmcl, 88% yield)NMR Spectroscopy: 1H NMR (700 MHz, (CD3)2S0, 25 C, 5): 8.08 (d, J =8.3 Hz, 1H), 7.92 (d, J = 7.7 Hz, lH), 7.81 (d, J = 7.7 Hz, 1H), 7.56-7.49 (m, 3H), 7.45-7.41 (m, 2H), 6.99 (s, 1H), 3.86 (s, 2H). C NMR(175 MHz, (CD)2SO, 25 C, 5): 172.1, 133.3, 132.9, 132.0, 128.3,127.8, 126.9, 125.9, 125.5, 125.5, 124.2. The 1H NMR data were in goodagreement with values reported in the literature (Tu, T. et al. 2012) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; | The intermediate 2-(1-naphthyl)ethylamine was prepared as follows. A suspension of 2-(1-napthyl)acetamide (1.85 g) in tetrahydrofuran (30 mL) was treated dropwise with lithium aluminum hydride (20 mL, 1.0M in THF). After gas evolution ceased, the mixture was heated to reflux for 2 hours, cooled to 0 C., treated dropwise with water (2.9 mL) and filtered. The liltrate was evaporated and purified by chromatography, eluding with chloroform:methanol:ammonium hydroxide (gradient, 100:0:0, 9:1:0, 9:1:0.1), to afford the product (0,240 g) as a semisolid; TLC: Rf =0.09, chloroform:methanol (95:5); MS: m/z=172(M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
As examples of plant growth regulants, which can preferably be present in the patch preparations according to the invention, there may be mentioned: ... sodium 5-chloro-3(1H)-indazolylacetate, ethyl 5-chloro-3(1H)-indazolylacetate, sodium 4-chloro-2-hy-droxymethylphenoxyacetate, triethanolamine (+-)-2-(2,4-dichlorophenoxy)-propionic acid, alpha-naphthylacetamide, p-chlorophenoxyacetic acid, 6-(N-benzylamino)-purine, 1-(2-chloro-4-pyridyl)-3-phenylurea, ... | ||
Such prior art compounds are for instance: ... indolyl-3-acetic acid, indolyl-3-butyric acid, alpha-naphthyl acetic acid, beta-naphthoxy acetic acid, naphthylacetamide, n-m-tolylphthalamido acid, gibberellins, S,S,S-tri-n-butyl-trithiophosphoric acid ester, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium hydrogensulfate; at 65℃; for 12h; | General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3h; | 3-BUTYNYL P-TOSYLATE Compound 2a (0.90 g, 4.0 MMOL) and 2-METHYLAMINOETHANOL (0.30 g, 4.0 mmol) were dissolved in DMF (2 mL) and sodium bicarbonate (0.34 g, 4.0 MMOL) was added. The mixture was heated to 75 C under argon for 2 h then cooled to rt and partitioned between DCM (30 mL) and saturated sodium bicarbonate (15 mL). The organic layer was washed once with sodium bicarbonate (15 mL), once with brine (10 mL), then dried (NA2SO4) and evaporated in vacuo to give Compound 2b as a colorless oil (0.98 g). Compound 2b was added to Compound 1b (0.43 g, 2.1 MMOL) followed by triphenyl phosphine (0.73 g, 2.8 MMOL) in THF (15 mL) and DIETHYLAZODICARBOXYLATE (0.49 g, 2.8 MMOL) and the mixture was stirred at ambient temperature for 1 h. The product was evaporated in vacuo to an oil, which was purified via flash column chromatography (ethyl acetate) to give Compound 2c (0.37 g, 56%) as a tan solid. ES-MS m/z 313 (MH+). A portion of the indole Compound 2c (34 mg, 0.11 MMOL) and 1-naphthalene acetamide (Compound 2d, 18 mg, 0.11 MMOL) in THF (1 mL) were treated with 1 M potassium t-butoxide in THF (0.33 mL, 0.33 MMOL) while being cooled in an ice bath. The mixture was stirred at ambient temperature for 3 h, then treated with 12 N HCI (0.15 mL), stirred for 10 min and evaporated in vacuo to give an oil. The oil was partitioned between chloroform and saturated sodium bicarbonate. The organic layer was washed again with saturated sodium bicarbonate, once with brine, then dried (NA2SO4) and evaporated in vacuo to give a mixture of Compound 17 and Compound 18 (50 mg) as an orange oil. The material was purified by preparative TLC to separate Compound 17 and Compound 18. Compound 17 : H NMR (CDCI3) 5 1.81 (s, 3 H), 2.31 (s, 3H), 2.81 (m, 2H), 3.30 (BD S, 2H), 4.22 (m, 2H), 6.18 (d, J=8. 0HZ, 1H), 6.52 (m, 1 H), 7.0 (m, 1 H), 7.15-8. 0 (m, 8H), 8.07 (s, 1 H) ; ES-MS M/Z 448 (MH+). Compound 18: 1H NMR (CDCI3) 61. 97 (m, 1 H), 2.24 (m, 2H), 2.29 (s, 3H), 2.61 (t, J = 7.3 Hz, 2H), 2.77 (m, 2H), 4.19 (m, 2H), 6.18 (d, J = 8.2 Hz, 1H), 6.51 (m, 1 H), 7.0 (m, 1 H), 7.20-7. 93 (m, 8H), 8.04 (s, 1 H) ; ES-MS M/Z 448 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.75h; | The methyl ester Compound 6d (0.2 g, 0.71 MMOL) and amide Compound 8a (94 mg, 0.51 MMOL) were combined in dry THF (5 mL) under argon and cooled in an ice bath as 1 M potassium t-butoxide in THF (2.5 mL, 2.5 mmol) was added with stirring over a 5 min period. After 40 min, the reaction was quenched in an ice bath while 12 N HCI (2 mL, 24 MMOL) was slowly added. The mixture was stirred for 15 min at rt, made slightly basic by the addition of 3N NAOH and extracted with EtOAc. The organic layers were combined and washed with saturated NAHC03 and brine, then dried (NA2SO4) and evaporated in vacuo to give a crude solid (0.25g). The solid was then purified by flash column chromatography (97: 3: 0.3 ; DCM: MeOH : NH40H) to afford Compound 30 (30 mg, 15%) as a yellow flaky solid. Compound 30 was dissolved in excess dilute HCI, then frozen and LYOPHILIZED to give the hydrochloride SALT. H NMR (CD30D) 8 9.22 (s, 1 H), 9.06 (s, 2H), 8.21 (s, 1 H), 7.99 (m, 1H), 7.90 (m, 1H), 7.77 (m, 1H), 7.53 (m, 2H), 7.39 (m, 3H), 7.05 (t, J = 7. 8 HZ, 1 H), 6.53 (t, J=7. 9HZ, 1H), 6.31 (d, J = 8.3 Hz, 1H). ES-MS m/z 417 (MH). |