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CAS No. : | 637-60-5 | MDL No. : | MFCD00012940 |
Formula : | C7H11ClN2 | Boiling Point : | - |
Linear Structure Formula : | CH3C6H4NHNH3Cl | InChI Key : | HMHWNJGOHUYVMD-UHFFFAOYSA-N |
M.W : | 158.63 | Pubchem ID : | 12504 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P301+P310-P305+P351+P338 | UN#: | 2811 |
Hazard Statements: | H301-H315-H319-H335 | Packing Group: | Ⅲ |
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 triethylamine; | EXAMPLE 3A 5-Amino-1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile In analogy to the preparation of Example 1A, 2.16 g (57percent of theory) of the desired product are obtained starting from 3 g (18.9 mmol) of 4-methylphenylhydrazine hydrochloride, 2.3 g (18.9 mmol) of ethoxymethylenemalononitrile and 7.9 ml (56.7 mmol) of triethylamine. LC-MS (Method 1): Rt=3.0 min. MS (ESI pos): m/z=199 (M+H)+. | |
General procedure: A stirred mixture of para-substituted phenylhydrazinehydrochloride (0.025 mol) was dissolved in H2O (30 mL), thenthe pH of the mixture was adjusted to pH 7?8 by the dropwiseaddition of 10percent NaOH solution to form the free para-substitutedphenyl hydrazines, which were then refluxed for 3 h with ethoxymethylene malononitrile in an ethanol medium. After completionof the reaction, the reaction mixture was allowed to cool at room temperature, and the solid were filtered under vacuum. The crudeproducts obtained were recrystallized from anhydrous ethanol togive the light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.7% | With potassium acetate; In acetic acid; for 6.0h;Reflux; | Example 10. Preparation of 3-(4-carboxybutyl)-2,3,5-trimethylindolenyne (compound 10) A mixture of 4-tolylhydrazine hydrochloride (compound 9) (825 mg; 5.2 mmole), glacial acetic acid (8 mL), 6-methyl-7-oxooctane acid (compound 5) (913 mg; 5.3 mmole), and anhydrous potassium acetate (980 mg; 10 mmole) was refluxed under stirring for 6 h. The solvent was removed, and the residue was dissolved in chloroform. The chloroform solution was washed with water, saturated solution of sodium chloride, and then dried over MgSO4. The solvent was removed and the residue was subjected to recrystallization from a mixture of diethyl ether - hexane, 1:10. 3-(4-Carboxybutyl)-2,3,5-trimethylindolenyne (compound 10) was obtained as a dark orange powder with yield of 1.13 g (83.7%). λmax 254 nm. Mass-spectrum (MALDI) (C16H21NO2): found m/z 260.7, calculated m/z 259.34. 1H-NMR (CDCl3), δ (ppm): 0.6-0.83 (2H, m, CH2CH2CH2CH2COOH); 1.25 (3H, s, 3-CH3); 1.46 (2H, m, CH2CH2CH2CH2COOH); 1.72-1.88 (2H, m, CH2CH2CH2CH2COOH); 2.09-2.18 (2H, m, CH2CH2CH2CH2COOH); 2.28 (3H, s, 2-CH3); 2.37 (3H, s, 5-CH3), 7,01-7.4 (3H, m, ArH), 10.11 (1H, s, COOH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2 Preparation of 1.2.3.4.5.6-hexahvdro-3.9-dimethylazepmor4.5-b1mdole[0367] The title compound was prepared by following general procedure 1 p-Tolyl hydrazine hydrochloride (15 g, 94 55 mmol) was taken into 7percent H2SO4 in 1,4-dioxane (650 mL), 1- methylazepan-4-one HCl (15 4 g, 94 55 mmol) was added and stirred at RT for 10 mm The reaction mixture was stirred at 800C for 14 h After completion of the reaction, reaction mass was slowly basified with 50percent NaOH solution, extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness and purified by column chromatography (silica gel 100-200 mesh, eluent 10percent methanol-DCM) to afford 3,9-dimethyl- l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole (5 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[146137-79-3]4-fluoro-3-formylbenzonitrile</strong> (1 eq) in DMF (0.32 M) was added p- tolylhydrazine hydrochloride (1.05 eq) and the suspension was irradiated in a microwave oven at 80 0C for 5 min. K2CO3 (2 eq) and DMF (up to 0.16 M concentration) were added and the suspension was irradiated in a microwave oven at 160 0C for 20 min. The mixture was then partitioned between EtOAc and brine, dried (Na2SO4), filtered and evaporated. The residue was purified by SCX cartridge, eluting with methanol. Evaporation of the solvent afforded compound Bl.MS (ES) Ci5HnN3 requires: 233, found: 234 (M+H)+.1H-NMR (300 MHz, OMSO-d6, 300K) delta: 8.52 (s, IH); 7.95 (s, IH); 7.98-7.86 (m, IH); 7.83-7.75 (m, IH); 7.64 (d, J= 8.2 Hz, 2H); 7.42 (d, J= 8.2 Hz, 2H); 2.40 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine; In ethanol; at 20 - 80℃; for 8.0h; | General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+]. |
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