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CAS No. : | 78025-93-1 | MDL No. : | MFCD20691409 |
Formula : | C9H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 167.21 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
(i) aq. HBr, NaNO2, (ii) CuBr, aq. HBr; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dioxane*Br2 2: NaNH2 / liquid ammonia | ||
Stage #1: 2,6-dimethoxytoluene With potassium amide; ammonia at -78℃; for 3.33333h; Stage #2: With ammonium chloride In water for 0.5h; Stage #3: With hydrogenchloride In water; toluene | 43 Example 43 3, 5-Dimethoxy-4-methyl-phenylamine To a freshly prepared suspension of potassium amide (from potassium 12.87 g, 330 mmol) in liquid ammonia (300 pL) held at-78°C was added example 9 (7.6 g, 33 mmol) dropwise over twenty minutes. The resulting suspension was stirred for a further 3 h and then excess potassium amide was quenched carefully with solid ammonium chloride (10 g) added portionwise over thirty minutes. Toluene (200 IlL) was added and the liquid ammonia allowed to evaporate. The organic solution was then washed with water (3 x 100 pL) before being shaken with hydrochloric acid (6 N, 200 IlL). The nascent precipitate was then collected by filtration and further washed with water (100 ; nL). The residue was stirred with sodium hydroxide (10 N, 100 IlL) for 1 h to form the free aniline, which was collected by filtration. The residues were washed with water (3 x 20 IlL) and dried in vacuo to give the title compound. | |
Multi-step reaction with 2 steps 1: dioxane dibromide / diethyl ether / 2 h 2: ammonia; potassium; ferric nitrate / tetrahydrofuran / 4 h / -78 - 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With palladium diacetate; potassium carbonate; XPhos; In 1,4-dioxane; water; at 100℃; for 21h;Inert atmosphere; Reflux; | A mixture of 4-chloro-3,5-dimethoxyani1ine (3.0 g, 16.0 mmol), paliadium(II)acetate(180 rug 0 80 rnmol) 2-didohcxvlphosphino-2 4 6 -tiusoptopylhiphenyl (XPhos) (381 mg, 0.80 mmol), potassium carbonate (6.73 g, 48.7 mmol) and methylboronic acid (1.15 g, 19.2 mmol) in water (100 mL) and dioxane (100 mL) was heated to 100C (oil bath temperature) under nitrogen for 18 h. The reaction was not complete and heated to reflux for an additional 3 h, cooled to room temperature, diluted with water (200 mL) andextracted with ethyl acetate (3 x 150 mL), dried over magnesium sulfate, concentrated and purified by flash chromatography (ethyl acetate/hexanes) to give 3,5- dimethoxy-4- methylaniline (720 mg, 27%). 1H NMR (400 MHz, CDC13) 5.93 (s, 2H), 3.77 (s, 6H), 3.58 (bs, 2H), 1.98 (s, 3H). Sodium nitrite (340 mg, 4.93 mmol) was added to a mixture of 3,5-dimethoxy-4-methylaniline (720 mg, 4.31 mmol) in sulfuric acid (1.1 mL) andwater (13 mL) at 0C and stirred for 30 mm. The ensuing mixture was added to a preheated mixture of sodium iodide (2.58 g, 17.2 mmol) and iodine (555 mg, 2.19 mmol) in sulfuric acid (1.1 mL) and water (13 mL) at 80C, and the mixture heated to reflux for 30 mm. The reaction mixture was cooled to room temperature and diluted with a solution of sodium sulfite (20% w/w, 100 mL) and water (100 mL), and extracted with ethylacetate (3 x 100 mL). The organics were combined, dried over magnesium sulfate, concentrated and purified by flash chromatography (ethyl acetate/hexanes) to give 5-iodo- 1,3-dimethoxy-2- methylbenzene as a white powder (388 mg, 32%). 1H NMR (400 MHz, CDC13) 6.84 (s, 2H), 3.79 (s, 6H), 2.02 (s, 3H). 5-Iodo-1,3-dimethoxy-2-methylbenzene (388 mg, 1.39 mmol) in dichloromethane (8 mL) was cooled to 0C before adding neatboron tribromide (0.8 mL, 8 mmol) slowly over 1 mm under nitrogen. The reaction mixture was allowed to warm to room temperature slowly over 3 h and stirred for 18 h. The reaction mixture was slowly and cautiously poured onto ice water (100 mL) and extracted with ethyl acetate (3 x 60 mL) and the combined organics washed with brine (1 x 50 mL), dried over magnesium sulfate, concentrated and purified by flashchromatography (ethyl acetate/hexanes) to give 5-iodo-2-methylbenzene-1,3-diol as a white powder (260 mg, 74%). 1H NMR (400 MHz, d6-DMSO) 9.44 (s, 2H), 6.63 (s, 2H), 1.87 (s, 3H). |