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Chemical Structure| 77375-19-0 Chemical Structure| 77375-19-0

Structure of 77375-19-0

Chemical Structure| 77375-19-0

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Product Details of [ 77375-19-0 ]

CAS No. :77375-19-0
Formula : C9H14ClNO
M.W : 187.67
SMILES Code : NC1=CC=C(OC)C(C)=C1C.[H]Cl
MDL No. :MFCD00130026

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Application In Synthesis of [ 77375-19-0 ]

* 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.

  • Downstream synthetic route of [ 77375-19-0 ]

[ 77375-19-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 81029-03-0 ]
  • [ 77375-19-0 ]
YieldReaction ConditionsOperation in experiment
98% With palladium on activated charcoal; hydrogen; In methanol; for 14.25h; A 250 ml. round bottom flask containing 1-methoxy-2,3-dimethyl-4-nitrobenzene (1 g, 5.52 mmol) was evacuated and back-filled with N2. The flask was then charged with Degussa grade Pd/C (0.5 87 g, 0.5 52 mmol). This mixture was carefully wet with afew milliliters of MeOH before the full solvent volume (27.6 ml) was added. The head space of the flask was evacuated until the solvent began to slightly bubble and then back-filled with N2. A balloon of hydrogen gas was attached and the mixture was sparged with H2 for about 15 minutes through a vent needle. The vent was removed and the reaction mixture was stir red vigorously under an atmosphere of H2 overnight. After14 h, the reaction mixture was filtered over celite and rinsed with EtOAc to afford Intermediate I-47B (820mg, 5.42 mmol, 98% yield) as a dark brown solid. This materialwas taken on to the next reaction without further purification. LC-MS: Method H, RT =0.71 mm, MS (ESI) m/z: 152.1 (M+H) ‘H NMR (400MHz, CHLOROFORM-d)6.66-6.47 (m, 2H), 3.75 (s, 3H), 3.34 (br. s., 2H), 2.17 (s, 3H), 2.10 (s, 3H).
92% With sodium tetrahydridoborate; ethanol; at 20℃; for 1h;Catalytic behavior; General procedure: This procedure includes the addition of Fe3O4 Guanidine-CuII (0.6 mol %) to nitro compound (1 mmol) and NaBH4(3 mmol) in ethanol (2 ml) within ambient conditionsand agitated for an appropriate period (Table 1).With the help of TLC, the advancement in reduction isregulated. Later, the catalyst particles were separated usingan external magnet, in addition to washing the mixturewith ethyl acetate (EtOAc) (2 × 5 ml) and H2O(3 × 5 ml).Then anhydrous Na2SO4was used to dehydrate the organiclayer and thus the solvent was evaporated to recover thecrude resultants with reduced pressure. The final step wasperformed by eluting the product with n-hexane: ethylacetate (4:1) solution in column chromatography packed with silica gel.
92% With sodium tetrahydridoborate; ethanol; at 20℃; for 1h;Catalytic behavior; General procedure: This procedure includes the addition of Fe3O4 Guanidine-CuII (0.6 mol %) to nitro compound (1 mmol) and NaBH4(3 mmol) in ethanol (2 ml) within ambient conditionsand agitated for an appropriate period (Table 1).With the help of TLC, the advancement in reduction isregulated. Later, the catalyst particles were separated usingan external magnet, in addition to washing the mixturewith ethyl acetate (EtOAc) (2 × 5 ml) and H2O(3 × 5 ml).Then anhydrous Na2SO4was used to dehydrate the organiclayer and thus the solvent was evaporated to recover thecrude resultants with reduced pressure. The final step wasperformed by eluting the product with n-hexane: ethylacetate (4:1) solution in column chromatography packed with silica gel.
70% palladium monocarbide; In ethanol; Reference Example 20 4-Methoxy-2,3-dimethylaniline <strong>[81029-03-0]4-Methoxy-2,3-dimethylnitrobenzene</strong> (21.1 g, 0.15 mol) was dissolved in ethanol (300 mL), and 10% palladium carbon (50% hydrate, 1.36 g) was added. The mixture was reacted at 40C for 2 hours under the hydrogen atmosphere. After cooled, the catalyst was removed, ethanol was distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The dilution was washed with 5% sodium hydrosulfite, dried over sodium sulfate, and purified by small amount silica gel column chromatography (ethyl acetate, 1:1). The solvent was distilled off under reduced pressure, followed by recrystallization from hexane, to obtain 15.8 g of the title compound. Yield 70% 1H-NMR (CDCl3) δ 2.10 (3H, s), 2.17 (3H, s), 2.95 (2H, br),3.75 (3H, s), 6.53 (1H, d, J = 8.6 Hz), 6.62 (1H, d, J = 8.6 Hz)
With hydrogen;palladium 10% on activated carbon; In ethyl acetate; under 3102.97 Torr; for 72h; Step 1: 4-Methoxy-2,3-dimethylaniline A Parr hydrogenation bottle was flushed with nitrogen, to which was added Pd/C (0.5 g, 10%), and a solution of 1-methoxy-2,3-dimethyl-4-nitrobenzene (10 g) in EtOAc (150 mL). The mixture was shaken under 60 psi of hydrogen for 3 days. Celite was added and the mixture was filtered through a Celite pad. The cake was washed with extra EtOAc. The combined organic phase was dried and evaporated to give 4-methoxy-2,3-dimethylaniline (7.2 g) as a brown solid, which was used further without further purification. 1H-NMR (300 MHz, CDCl3), δ=6.65-6.58 (d, J=8.66 Hz, 1H); 6.58-6.49 (d, 1H); 3.75 (s, 3H); 2.35 (s, 2H); 2.17 (s, 3H); 2.10 (s, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=151.23, 138.29, 126.07, 123.4, 112.95, 109.48, 56.48, 13.51, 12.28 ppm.
With hydrogen; In ethanol; at 40℃; for 1.33333h;Autoclave; Example 15: Take 24.6ml H2PtCl6· 6H2O(0.01mol/L)34.2ml RhCl3 (0.01mol / L) 43.8ml Cu (NO3)2· 3H2O solution (0.03mol / L), were weighed 1.032g of silicon carbide were mixed and stirred at room temperature for 12h, evaporated to dryness, and then dried at 110 deg.] C 12h, and finally placed in a tube furnace at 500 under with H2/ Ar (5:95) reducing 5h, gas flow rate was 20mL / min, the loading of platinum was obtained 1.2g 4wt%, rhodium 3wt%, copper metallic platinum supported 7wt% silicon carbide - rhodium - copper catalyst, wherein the platinum - rhodium - Cu ternary metal nanoparticle particle size of 51 nm.9 g of <strong>[81029-03-0]2,3-dimethyl-4-nitroanisole</strong> and 40 mL of absolute ethanol were mixed at a mass ratio of 0.28, 0.2 g of the above catalyst (catalyst and 2,3-dimethyl-4-nitro Anodic acid mass ratio of 0.02) to form a suspension and then transferred to a high pressure autoclave with a quartz window. The reactor was sealed and purged with hydrogen to maintain the flow rate of hydrogen at atmospheric pressure at 40111171] 1; [11 (801] 1; [11 in the total feed gas and <strong>[81029-03-0]2,3-dimethyl-4-nitroanisole</strong> molar ratio of 2.88), under stirring conditions, heating reaction system To 40 C, the intensity of 1.7W / cm2 simulated sunlight under the artificial light irradiation reaction, the reaction time 80min. Wherein the conversion of <strong>[81029-03-0]2,3-dimethyl-4-nitroanisole</strong> was 93% and the selectivity of 2,3-dimethyl-4-aminoanisole was 88%.

 

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