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CAS No. : | 110102-86-8 | MDL No. : | MFCD09744010 |
Formula : | C7H8ClNO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 157.60 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | 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 |
---|---|---|
With sodium bicarbonate; In ethanol; water; | 2. 2-methyl-4-chloro-5-ethylaminophenol (novel compound) A mixture of 3 g of 4-chloro-2-methyl-5-aminophenol (0.016 mol), 2.6 g of ethyliodide (0.017 mol), 1.35 g of sodium hydrogen carbonate (0.016 mol) and 30 ml of ethanol was refluxed for 7 hours. After cooling and dilution with 50 ml of water, the solution was neutralized with a sodium hydrogen carbonate solution and then extracted three times with 50 ml of ethylacetate. The extract was dried over sodium sulfate and concentrated to dryness. The residue was recrystallized from toluene. Beige crystals melting at 205 C. were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In acetonitrile;Heating; | General procedure: 4-Chloro-6,7-dimethoxyquinazoline 3 and the required nucleophile were heated in solvent either thermally or using microwave heating until no further reaction was observed. On cooling, the hydrochloride salt was isolated by filtration. Alternative isolation procedures were employed if precipitation did not occur. Additional purification by preparative HPLC or flash column chromatography was employed in some cases. Spectroscopic data for compounds 4 [13], 6-9 [14-16], 20-21 [13], 25 [13], 28 [17] and 30 [18] are in agreement with those reported in the literature. 5.1.1.18 4-Chloro-5-((6,7-dimethoxyquinazolin-4-yl)amino)-2-methylphenol hydrochloride (31) A mixture of 3 (142 mg, 0.63 mmol) and <strong>[110102-86-8]5-amino-4-chloro-2-methyl-phenol</strong> (100 mg, 0.63 mmol) in MeCN returned the crude product which was recrystallized from DCM/MeOH to afford 31 (215 mg, 89%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.17 (br s, 1H), 9.99 (br s, 1H), 8.76 (s, 1H), 8.11 (br s, 1H), 7.25-7.36 (m, 2H), 6.91 (s, 1H), 4.01 (s, 3H), 3.99 (s, 3H), 2.18 (s, 3H). |