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CAS No. : | 36112-61-5 | MDL No. : | MFCD00090331 |
Formula : | C12H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WRZAWKSSADRYTA-UHFFFAOYSA-N |
M.W : | 202.21 | Pubchem ID : | 4413708 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With aluminum (III) chloride; In chlorobenzene; at 35 - 80℃; for 24h;Catalytic behavior; | In a 250ml four-necked bottle, add 20g of furoic acid, 23.2g of anisole, 100ml chlorobenzene, stirred and mixed; oil bath heated to internal temperature 35 ~ 40 C, slowly added 55.9g anhydrous aluminum trichloride; after the completion of the feed, stirring at 75-80 C for about 24 hours; cooling, concentrated distillation under reduced pressure Chlorobenzene After the distillation was completed, the temperature was lowered to room temperature, 60 ml of N,N-dimethylformamide was added to the reaction flask, and the mixture was stirred and mixed. At room temperature, 32.1 g of anhydrous aluminum trichloride was slowly and separately added; after the completion of the feeding, the oil bath was heated to The internal temperature is 135 C, and the reaction is kept for 6 hours; The water is cooled to room temperature; the reaction solution is slowly added to dilute hydrochloric acid solution for hydrolysis; extracted with ethyl acetate several times, and the ethyl acetate extract is combined, washed with water, and Ph is weakly acidic; The organic layer was concentrated under reduced pressure to recover ethyl acetate; The residue is decolorized and recrystallized with dilute alcohol water. Yielding 19.7 g of 6-hydroxy-1-naphthoic acid as a gray to pale yellow powder. Yield: 58.7%, melting point: 205.5 to 208.6 C, purity: 98.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.7 g | With aluminum (III) chloride; In N,N-dimethyl-formamide; at 135℃; for 6h; | In a 250ml four-necked bottle, add 20g of furoic acid, 23.2g of anisole, 100ml chlorobenzene, stirred and mixed; oil bath heated to internal temperature 35 ~ 40 C, slowly added 55.9g anhydrous aluminum trichloride; after the completion of the feed, stirring at 75-80 C for about 24 hours; cooling, concentrated distillation under reduced pressure Chlorobenzene After the distillation was completed, the temperature was lowered to room temperature, 60 ml of N,N-dimethylformamide was added to the reaction flask, and the mixture was stirred and mixed. At room temperature, 32.1 g of anhydrous aluminum trichloride was slowly and separately added; after the completion of the feeding, the oil bath was heated to The internal temperature is 135 C, and the reaction is kept for 6 hours; The water is cooled to room temperature; the reaction solution is slowly added to dilute hydrochloric acid solution for hydrolysis; extracted with ethyl acetate several times, and the ethyl acetate extract is combined, washed with water, and Ph is weakly acidic; The organic layer was concentrated under reduced pressure to recover ethyl acetate; The residue is decolorized and recrystallized with dilute alcohol water. Yielding 19.7 g of 6-hydroxy-1-naphthoic acid as a gray to pale yellow powder. Yield: 58.7%, melting point: 205.5 to 208.6 C, purity: 98.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxalyl dichloride; In dichloromethane; at 20℃; for 2h;Heating / reflux; | To a solution of 0.18 g (0.90 mmol) of <strong>[36112-61-5]6-methoxy-1-naphthoic acid</strong> (35) in 10 mL of dichloromethane was added dropwise 0.44 ml (5.0 mmol) of oxalyl chloride. The solution was stirred at room temperature for 1 h, then heated at reflux for 1 h. After cooling, the solvent and residual oxalyl chloride were removed in vacuo. The residue was dissolved in 5 mL of toluene and added to a solution of 0.20 g (1.3 mmol) of 1-propylindole in 4 mL of toluene at 0 C. To this solution was added dropwise 0.82 mL (1.5 mmol) of 1.8 M EtAlCl2. The mixture was allowed to warm to ambient temperature and stirred for 18 h. After quenching with water, the reaction mixture was extracted with ether. The ethereal extracts were washed with water, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed (petroleum ether:ethyl acetate, 8:1) to give 0.19 g of JWH-163 as a colorless solid: m.p. 139-140 C.; 1H NMR (300 MHz, CDCl3) delta 0.87 (t, J=7.3 Hz, 3H), 1.81 (sextet, J=7.3 Hz, 2H), 3.91 (s, 3H), 4.01 (t, J=7.2 Hz, 2H), 7.12 (dd, J=9.0, 2.5 Hz, 1H), 7.18 (d, J=2.5 Hz, 1H), 7.30-7.39 (m, 4H), 7.44-7.52 (m, 2H), 7.82 (dd, J=7.5, 1.6 Hz, 1H), 8.09 (d, J=9.0 Hz, 1H), 8.47-8.50 (m, 1H); 13C NMR (75.5 MHz, CDCl3) delta 11.3,23.0,48.7,55.2, 106.0, 110.0, 117.4, 119.3, 122.7, 122.8, 123.5, 123.6, 125.1, 126.1, 126.9, 127.5, 128.7, 135.1, 137.0, 138.0, 139.0, 157.7, 192.1; Anal. Calcd for C23H21NO2: C, 80.44; H, 6.16; N, 4.08; Found: C, 80.30; H, 6.17; N, 3.99. | |
With thionyl chloride; for 3h;Inert atmosphere; Reflux; | Under an argon atmosphere, <strong>[36112-61-5]6-methoxy-1-naphthoic acid</strong> (synthesized by the process of J. D. Moseley and J. P. Gilday, Tetrahedron, 62, 4690-4697 (2006)) (1.20 g, 5.93 mmol) was dissolved in thionyl chloride (5.00 mL, 68.8 mmol) and the solution was heated to reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude product of 6-methoxy-1-naphthoyl chloride (22) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In diethyl ether; at 0℃; for 40h;Inert atmosphere; | Method E: to a solution of compound 9a (667 mg, 3.30 mmol) inanhydrous Et2O (40 mL) stirred at 0 C under argon was slowlyadded a 1.6 M methyllithium solution (8.26 mL, 13.20 mmol). Theresulting solution was stirred at 0 C for 16 h. After that, two supplementary equivalents of the methyllithium solution were addedand the mixture was stirred at 0 C for additional 24 h. The reactionwas quenched with a saturated ammonium chloride solution andextracted with Et2O. The combined organic layers were dried overMgSO4, filtered, and evaporated under reduced pressure. A purification by silica column chromatography using CH2Cl2 as eluentgave the desired ketone 10a (324 mg, 49%) as an orange oil.1H NMR (300 MHz, CDCl3) d 8.69 (d, 1H, J 9.3 Hz, H8), 7.89 (dd,1H, J 8.4, 1.2 Hz, H2), 7.81 (dd, 1H, J 7.5, 1.2 Hz, H4), 7.46 (dd, 1H,J 8.4, 7.5 Hz, H3), 7.27 (dd, 1H, J 9.3, 2.7 Hz, H7), 7.16 (d, 1H,J 2.7 Hz, H5), 3.93 (s, 3H, CH3O), 2.74 (s, 3H, CH3CO). 13C NMR(75 MHz, CDCl3) d 201.9,157.6,135.5,135.2,131.8,127.6,126.5,125.5,124.9, 120.4, 106.3, 55.2, 29.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | To a solution of 0.96 g (3.18 mmol) of 6-methoxy-1-naphthyl trifluoromethanesulfonate in 30 mL of DMF was added 0.034 g (0.15 mmol) of Pd(OAc)2, 0.040 g (0.010 mmol) of 1,3-bis(diphenylphosphino)propane and 1.20 g of triethylamine. The mixture was flushed with carbon monoxide for 25 min, 3.1 mL of 96% formic acid was added dropwise and the reaction was stirred at ambient temperature for 6 h under an atmosphere of CO, diluted with water and extracted with ethyl acetate. The organic extracts were washed with five portions of brine, followed by two portions of aqueous NaHCO3. The bicarbonate extracts were combined, cautiously neutralized with 10% aqueous HCl, and extracted with ether. The ethereal extracts were washed with water, dried (MgSO4) and the solvent was removed in vacuo to give 0.42 g (65%) of acid 35 as a yellow powder. Recrystallization from ethyl acetate:petroleum ether gave pale yellow needles: m.p. 185-186 (lit mp 180-180.5 C., ref. 36); 1H NMR (300 MHz, CDCl3) delta 3.89 (s, 3H), 7.29 (dd, J=6.9, 2.4 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.53 (t, J=7.8 Hz, 1H), 7.98 (d, J=6.1 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.79 (d, J=9.1 Hz, 1H); 13C NMR (75.5 MHz, CDCl3) delta 55.2, 106.7, 120.0, 125.4, 126.1, 127.1, 127.5, 127.6, 131.8, 135.2, 157.1, 168.8; MS (EI) m/z 202 (100), 159 (35), 109 (50). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 6-Methoxy-1-naphthoylguanidine hydrochloride Analogously to Example 2, 1.2 g of 6-methoxy-1-naphthoylguanidine hydrochloride were obtained from 2.0 g of <strong>[36112-61-5]6-methoxy-1-naphthoic acid</strong>; m.p.: 235-236 C. 1H-NMR (DMSO-d6): delta [ppm]=3.9 (3H), 7.3 (1H), 7.5 (1H), 7.6 (1H), 7.85 (1H), 8.1 (1H), 8.25 (1H), 8.6 (4H), 12.0 (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
208 g (96%, based on 6-hydroxy-1-naphthoic acid employed) | 208 g (96%, based on 6-hydroxy-1-naphthoic acid employed) (the total yield of methyl 6-methoxy-1-naphthoate and 6-methoxy-1-naphthoic acid, based on the mixture of 6-hydroxy- and 6-methoxy-1-naphthoic acid employed, is 98%) Pure substance content: >99% (GC) Melting point: 44 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | To a solution of <strong>[36112-61-5]6-methoxy-1-naphthalenecarboxylic acid</strong> (129 mg, 0.64 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.28 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml) were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (150 mg, 0.43 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml), and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and recrystallized from ethyl acetate-hexane to give the title co! mpound (148 mg, 69%). mp 193-194C IR nu maxKBrcm-1: 1636, 1512. Anal. Calcd for C26H23F4NO3·0.1H2O: C, 67.36; H, 4.68; N, 2.81 Found: C, 67.24; H, 4.71; N, 2.81.1H-NMR (CDCl3)delta: 2.80-3.16 (2H, m), 3.37 (1H, brs), 3.91 (3H, s), 4.70-4.90 (1H, m), 5.09 (1H, brs), 5.95 (1H, d, J = 8.4 Hz), 6.98-7.18 (5H, m), 7.20-7.40 (3H, m), 7.40-7.60 (5H, m), 7.75 (1H, d, J = 8.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium hydroxide; In tetrahydrofuran; water; at 100℃; for 4h; | Method D: to a solution of compound 8a (1.70 g, 7.87 mmol) inTHF (6 mL) was added a 85% aqueous potassium hydroxide solution(3 mL). The mixture was stirred at 100 C for 4 h, cooled to roomtemperature, and acidified with a 1 M HCl solution. The resultingprecipitate was filtered and washed with water to afford thedesired acid 9a (1.51 g, 95%) as a-pink solid.Mp 95.3 C. 1H NMR (300 MHz, DMSO-d6) d 8.77 (d, 1H,J 9.3 Hz, H8), 8.04 (dd, 1H, J 8.1, 1.2 Hz, H2), 7.97 (dd, 1H, J 8.4,1.2 Hz, H4), 7.53 (dd, 1H, J 8.4, 8.1 Hz, H3), 7.42 (d, 1H, J 2.7 Hz,H5), 7.28 (dd, 1H, J 9.3, 2.7 Hz, H7), 3.89 (s, 3H, CH3). 13C NMR(75 MHz, DMSO-d6) d 168.8, 157.1, 135.2, 131.9, 127.7, 127.5, 127.2,126.1, 125.5, 120.0, 106.7, 55.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | The 250 ml of toluene and 50 g of 6- methoxy - 1-naphthoic acid were added in a 1L three-necked flask and cool to below 10 C with stirring. 32 ml of thionyl chloride and 1 ml of N,N- dimethylformamide was added dropwise. Heated to 40 C and stirred for 4 h. The reaction was concentrated to give 54g of a yellow oil. 100 ml of toluene, 54 g of the above yellow oil and 80 ml of triethylamine were added to a 2 L three-necked flask with stirring and cooled to 10 C. A 29.2 g (R) - (+) ethyl 2-hydroxypropionate dissolved in 150 ml of toluene was added dropwise and the mixture was stirred at room temperature for 2 hours. Slowly the 10% citric acid solution 200 ml was added, and let stand stratification. The toluene layer was washed with 50 ml of saturated aqueous sodium chloride solution. The toluene layer was dried over anhydrous sodium sulfate. Filter, filter cake washed with toluene. The filtrate was concentrated to 69 g of a yellow oil ( compound III ), (R)- [1-ethoxy-1-carbonylpropan-2-yl] -6- methoxy -1- naphthoic acid ester, yield 92%. |
Tags: 36112-61-5 synthesis path| 36112-61-5 SDS| 36112-61-5 COA| 36112-61-5 purity| 36112-61-5 application| 36112-61-5 NMR| 36112-61-5 COA| 36112-61-5 structure
[ 62089-34-3 ]
3-Methoxy-5-methylbenzoic acid
Similarity: 0.93
[ 62089-34-3 ]
3-Methoxy-5-methylbenzoic acid
Similarity: 0.93
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