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CAS No. : | 194413-58-6 | MDL No. : | MFCD09763655 |
Formula : | C15H14N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUWDLXZGHZSWQZ-WQLSENKSSA-N |
M.W : | 238.28 | Pubchem ID : | 5329098 |
Synonyms : |
(Z)-SU5416
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
86% | With piperidine In methanolReflux | General procedure: To a solution of indolin-2-one (compound 1) (200 mg, 1eq.) in MeOH (5 mL), piperidine (1.5 eq.), and correspondingaldehydes (2a–2k) (1.2 eq.) were added. Thereaction mixture was heated to reflux and stirred for 1–4 h,then cooled to room temperature. The mixture was filtered,and the filter cake was washed with MeOH three times, thenthe filter cake was collected and dried under vacuum toremove MeOH to give the desired compounds 3a–3k. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With piperidine; In methanol;Reflux; | General procedure: To a solution of indolin-2-one (compound 1) (200 mg, 1eq.) in MeOH (5 mL), piperidine (1.5 eq.), and correspondingaldehydes (2a-2k) (1.2 eq.) were added. Thereaction mixture was heated to reflux and stirred for 1-4 h,then cooled to room temperature. The mixture was filtered,and the filter cake was washed with MeOH three times, thenthe filter cake was collected and dried under vacuum toremove MeOH to give the desired compounds 3a-3k. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; In methanol; | Example 206 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(1-pyrrolidinylmethyl)-1,3-dihydro-2H-indol-2-one Pyrrolidine (450 mg, 6.3 mmol) was added to a stirred solution of aqueous formaldehyde (500 mg of 38% solution, 6.0 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one, (900 mg, 3.8 mmol) in methanol (50 mL). After 15 min, the solution was cooled to 0 C. and the precipitate was filtered off, washed with water, and dried to give 1.08 g of the title compound, mp 129-132 C. HPLC Rt 4.87 min. 1H NMR [(CD3)2SO] delta 1.65 (m, 4H), 2.32 (s, 3H), 2.34 (s, 3H), 2.62 (m, 4H), 4.72 (s, 2H) 6.07 (d, 1H), 7.00 (m, 1H), 7.15 (m, 2H), 7.61 (s, 1H), 7.76 (d, 2H) and 13.1 (br s, 1H). Anal. Calcd for C20H23N3O: C, 74.74; H, 7.21; N, 13.07. Found: C, 74.61; H, 7.25; N, 13.03. | |
With formaldehyd; In methanol; | Example 2 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene)-1-(1-pyrrolidinylmethyl)-1,3-dihydro-2H-indol-2-one Pyrrolidine (450 mg, 6.3 mmol) was added to a stirred solution of aqueous formaldehyde (500 mg of 38% solution, 6.0 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (900 mg, 3.8 mmol) in methanol (50 mL). After 15 min., the solution was cooled to 0 C. and the precipitate was filtered off, washed with water, and dried to give 1.08 g of the title compound, mp 129-132 C. HPLC Rt 4.87 min. 1H NMR [(CD3)2SO] delta1.65 (m, 4H), 2.32 9s, 3H), 2.34 (s, 3H), 2.62 (m, 4H), 4.72 (s, 2H) 6.07 (d, 1H), 7.00 (m, 1H), 7.15 (m, 2H), 7.61 (s, 1H), 7.76 (d, 2H) and 13.1 (br s, 1H). Anal. Calcd for C20H23N3O: C, 74.74; H, 7.21; N, 13.07. Found: C, 74.61; H, 7.25; N, 13.03. | |
With formaldehyd; In methanol; | Example 14 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(1-pyrrolidinylmethyl)-1,3-dihydro-2H-indol-2-one Pyrrolidine (450 mg, 6.3 mmol) was added to a stirred solution of aqueous formaldehyde (500 mg of 38% solution, 6.0 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one, (900 mg, 3.8 mmol) in methanol (50 mL). After 15 min, the solution was cooled to 0 C. and the precipitate was filtered off, washed with water, and dried to give 1.08 g of the title compound, mp 129-132 C. HPLC Rt 4.87 min. 1H NMR [(CD3)2SO]delta1.65 (m, 4H), 2.32 9s, 3H), 2.34 (s, 3H), 2.62 (m, 4H), 4.72 (s, 2H) 6.07 (d, 1H), 7.00 (m, 1H), 7.15 (m, 2H), 7.61 (s, 1H), 7.76 (d, 2H) and 13.1 (br s, 1H). Anal. Calcd for C20H23N3O: C, 74.74; H, 7.21; N, 13.07. Found: C, 74.61; H, 7.25; N, 13.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; In methanol; | Example 205 (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-[1-(4-methylpiperazinyl)methyl]-1,3-dihydro-2H-indol-2-one N-Methylpiperazine (10 g, 100 mmol) was added to a stirred solution of aqueous formaldehyde (10 g of 38% solution, 100 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one, (2.38 g, 10 mmol) in methanol (100 mL). The solution heated at 60 C. for 1 h, concentrated to a low volume and the precipitate was filtered off, washed with methanol, and dried to give 2.38 g of the title compound, mp 160-164 C. HPLC Rt 4.72 min. 1H NMR (CDCl3) delta 2.26 (s, 3H), 2.33 (s, 3H), 2.38 (s, 3H), 2.43 (br s, 4H), 2.70 (br s, 4H), 4.59 (s, 2H), 5.96 (d, 1H), 7.02-7.08 (m, 2H), 7.15 (dd, 1H), 7.38 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C21H26N4O: C, 71.97; H, 7.48; N, 15.99. Found: C, 71.75; H, 7.46; N, 15.87. | |
With formaldehyd; In methanol; | Example 13 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-[1 -(4-methylpiperazinyl)methyl]-1,3-dihydro-2H-indol-2-one N-Methylpiperazine (10 g, 100 mmol) was added to a stirred solution of aqueous formaldehyde (10 g of 38% solution, 100 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one, (2.38 g, 10 mmol) in methanol (100 mL). The solution heated at 60 C. for 1 h, concentrated to a low volume and the precipitate was filtered off, washed with methanol, and dried to give 2.38 g of the title compound, mp 160-164 C. HPLC Rt 4.72 min. 1H NMR (CDCl3) delta2.26 (s, 3H), 2.33 (s, 3H), 2.38 (s, 3H), 2.43 (br s, 4H), 2.70 (br s, 4H), 4.59 (s, 2H), 5.96 (d, 1H), 7.02-7.08 (m, 2H), 7.15 (dd, 1H), 7.38 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C21H26N4O: C, 71.97; H, 7.48; N, 15.99. Found: C, 71.75; H, 7.46; N, 15.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 gram (89%) | With CDI; In N,N-dimethyl-formamide; | Example 2 Synthesis of 3-[1-(3,5-Dimethyl-1H-Pyrrol-2-yl)-Meth-(Z)-Ylidene]-1-(Imidazol-1-Ylcarbonyl)-1,3-Dihydro-Indol-2-One A reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole (1.0 gram, 4.2 mmol) and CDI (1.36 gram 8.4 mmol) in DMF was stirred at room temperature for 2 h and filtered. The precipitate was washed with DMF and dried in a high vacuum oven to give 1.25 gram (89%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one as an orange solid. 1H-NMR (400 MHz, DMSO-d6) delta 12.23 (s, 1H, NH-1'), 8.45 (s, 1H), 7.94 (m, 1H), 7.79 (m, 1H), 7.73 (s, 1H, H-vinyl), 7.46 (m, 1H), 7.25 (m, 2H), 7.13 (m, 1H), 6.14 (d, J=1.95 Hz, 1H, H-4'), 2.36 (s, 3H, CH3), and 2.32 (s, 3H, CH3). MS m/z (relative intensity, %) 332 (100, M+.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With HCl aq.; In tetrahydrofuran; | Example 1 Synthesis of 3-[1-(3,5-Dimethyl-1H-Pyrrol-2-yl)-Meth-(Z)-Ylidene]-2-oxo-2,3-Dihydro-Indole-1-Carbonyl Chloride To the solution of triphosgene (7.2 gram, 24.2 mmol) in 500 mL of anhydrous THF was added 56 mL of thiethylamine in one portion and the resulting mixture was stirred at room temperature for 10 minutes. Solid 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole (5.768 gram, 24.2 mmol) was added in one portion to the above mixture. The reaction mixture was stirred at room temperature for 1 h and then cooled on ice bath to 0-4 C. Ice-cold 4M HCl aq. (1.5 L) was added in one portion upon vigorous stirring. The resulting suspension was further stirred for 10 min., and filtered. The solid was washed with ice-cold 4M HCl aq. and dried on the high vacuum oven overnight. The crude product was recrystallized from anhydrous benzene and filtered. The solid was then washed with cyclohexane and dried in a vacuum oven overnight to yield 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride (5.531 gram, 76%). 1H-NMR (400 MHz, DMSO-d6) delta 12.41 (s, br, 1H), 7.98 (m, 1H), 7.52 (m, 1H), 7.43 (s, 1H), 7.25 (m, 1H), 6.08 (d, br, J=2 Hz, 1H), 2.43 (s, 3H), 2.36 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; triethylamine; In N-methyl-acetamide; | Example 3 Synthesis of 1-({(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-2-oxo-1,3-dihydro-1H-indol-1-yl} methyl)pyridinium Chloride Aqueous formaldehyde (15.0 g of 38% solution, 190 mmol) was added to a stirred solution of 3(Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1,3-dihydro-2H-indol-2-one (23.8 g, 100 mmol) and triethylamine (15.0 g, 150 mmol) in dimethylformamide (200 mL). After 1 h, the solution was diluted with water and the precipitate was filtered off, washed with water, and dried to give 26.4 g of 3(Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one, mp 196-200 C. HPLC Rt 5.71 min. 1H NMR (CDCl3) delta2.34 (s, 6H), 3.14 (t, 1H), 5.44 (d, 2H), 5.98 (d, 1H), 7.08 (m, 2H), 7.18 (m, 1H), 7.36 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C16H16N2O2: C, 71.62; H, 6.01; N, 10.44. Found: C, 71.33; H, 6.09; N, 10.43. | |
With formaldehyd; triethylamine; In N-methyl-acetamide; | Example 1 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one Aqueous formaldehyde (15.0 g of 38% solution, 190 mmol) was added to a stirred solution of 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (23.8 g, 100 mmol) and triethylamine (15.0 g, 150 mmol) in dimethylformamide (200 mL). After 1 h, the solution was diluted with water and the precipitate was filtered off, washed with water, and dried to give 26.4 g of the title compound, mp 196-200 C. HPLC Rt 5.71 min. 1H NMR (CDCl3) delta2.34 (s, 6H), 3.14 (t, 1H), 5.44 (d, 2H), 5.98 (d, 1H), 7.08 (m, 2H), 7.18 (m, 1H), 7.36 (s, 1H), 7.48 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C16H16N2O2: C, 71.62; H, 6.01; N, 10.44. Found: C, 71.33; H, 6.09; N, 10.43. A sample was recrystallized from ethyl acetate; mp 200-202 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
136.7 mg (57%) | In ethanol; | 5.12. Synthesis of 3-[(2,4-Dimethylpyrrol-5-yl)methylene]-2-indolinone (SU5416) A reaction mixture of 134.0 mg of oxindole, 147.8 mg of the 3,5-dimethylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90 C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 136.7 mg (57%) of the title compound as a yellow solid. |
136.7 mg (57%) | In ethanol; | 12. Synthesis of 3-[(2,4-Dimethylpyrrol-5-yl)methylene]-2-indolinone A reaction mixture of 134.0 mg of oxindole, 147.8 mg of the 3,5-dimethylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90 C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 136.7 mg (57%) of the title compound as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; In N,N-dimethyl-formamide; | Example 19 Synthesis of benzyl 2-{(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2-oxo-2,3-dihydro-1H-indol-1-yl}-2-oxoethylcarbamate A mixture of N-(benzyloxycarbonyl)glycine (4.9 g, 23 mmol), 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (2.38 g, 10 mmol), dimethylaminopyridine (1.28 g, 10 mmol) in DMF (20 mL) was heated at 55 C. for 2 h. The solution was cooled, ether (10 mL) was added and the precipitate of the title compound was filtered off and dried to give 2.35 g, mp 193-196 C. HPLC Rt 7.04 min. 1H NMR (CDCl3) delta2.34 (s, 3H), 2.42 (s, 3H), 4.87 (d, 2H), 5.18 (s, 2H), 5.74 (t, 1H), 6.06 (d, 1H), 7.2 (m, 3H), 7.3-7-65 (m, 7H), 7.49 (m, 1H), and 8.23 (m, 1H). Anal. Calcd for C25H23N3O: C, 69.92; H, 5.40; N, 9.78. Found: C, 69.91; H, 5.50; N, 9.86. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride; triethylamine; In N,N-dimethyl-formamide; | Example 4 Synthesis of 1-{(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-2-oxo-2,3-dihydro-1H-indol-1-yl}ethyl acetate A mixture of acetic anhydride (2.1 g, 20 mmol), acetaldehyde (4.4 g, 100 mmol), triethylamine (2.0 g, 20 mmol) and 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylidene)-1,3-dihydro-indol-2-one (2.38 g, 10 mmol) in DMF (30 mL) was stirred at room temperature for 3 days. The solvents were removed and the residual oil was chromatographed on silica gel to give, as the first product eluted from the column, 2.5 g of product, which was crystallized from ether to give 2.1 g of the title compound, mp 107-110 C. HPLC Rt 6.78 min. 1H NMR (CDCl3) delta1.81 (d, 3H), 2.09 (s, 3H), 2.33 (s, 3H), 2.38 (s, 3H), 5.98 (s, 2H), 7.00-7.20 (m, 3H), 7.25 (dd, 1H), 7.39 (s, 1H), 7.51 (dd, 1H) and 13.0 (br s, 1H). Anal. Calcd for C19H20N2O3: C, 70.35; H, 6.21; N, 8.64. Found: C, 70.33; H, 6.18; N, 8.60. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With n-butyllithium; In tetrahydrofuran; hexane; | Example 21 Synthesis of (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1-(dimethylphosphoryl)-1,3-dihydro-2H-indol-2-one (3Z)-3 -[(3,5-dimethyl-1H-pyrrol-2-yl)-methylidene]-1,3-dihydro-2H-indol-2-one (521 mg, 2.19 mmol) was dissolved in THF (60 ml). The reaction mixture was cooled to -78 C. Butyllithium (2.7 ml, 4.32 mmol; 1.6 M in hexane) was added dropwise followed by the dropwise addition of dimethyl chlorophosphate (0.46 ml, 4.27 mmol). The reaction mixture was stirred for 1 h at -78 C., then the mixture was allowed to warm to 0 C. during 4 h. The reaction mixture was poured into ice water and extracted with EtOAc (2*). The organic layers were washed with brine and dried over sodiumsulfate. The solvent was removed and the residue was purified by silica gel chromatography (CH2Cl2/EtOAc: 10/1; 250 ml; CH2Cl2/EtOAc: 3/1; 300 ml) to yield the title compound as a red solid (87%). 1H NMR (400 MHz, d6-DMSO) delta2.35 (s, 3H), 2.38 (s, 3H), 3.80 (d, J=12.1 Hz, 6H), 6.12 (d, J=2.3 Hz, 1H), 7.13-7.20 (m, 2H), 7.67 (d, J=1.2 Hz, IH), 7.71 (dd, J=2.0, 7.2 Hz, 1H), 7.84 (dd, J=2.0, 7.0 Hz, 1H), 12.64 (s, 1H); 31P NMR (162 MHz, d6-DMSO) delta-1.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14%; 80% | With iron; acetic acid; In ethanol; water; at 20℃; for 1.0h;Sonication; | General procedure: A mixture of 2 (0.030 g, 0.058 mmol) and Fe(0) (0.033 g, 0.584 mmol) wasdissolved in 6 mL CH3COOH:EtOH:H2O (1:1:1) and sonicated for 1 hour at room temperature. After consumption of starting material (TLC analysis), the reaction was filtered through celite and washed with EtOH (30 mL). The mixture was concentrated under vacuum and redissolved in Et2O (30 mL). The organic layer was extracted with 1 M NaOH(aq) (3 × 30 mL). The organic and aqueous layers were separated. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 3. The aqueous layer was acidified with 1 M HCl(aq) (100 mL) and extracted with Et2O (2 × 30 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 16. The crude products were purified by preparative TLC (20% acetone:80% pet. spirit) to yield 3 as a yellow solid (11.6mg, 84%) and 16 as a yellow solid (1.6 mg, 11). The same procedure with1yielded 3 (11.4 mg, 80.0 %) and 16 (2.1 mg, 14 %). |
37%; 43% | With sodium tetrahydroborate; palladium on activated charcoal; In methanol; water; at 20℃; for 0.5h; | General procedure: A mixture of 2 (0.030 g, 0.058 mmol), NaBH4 (0.022 g, 0.582 mmol) and Pd-C (0.020 g) was dissolved in 6 mL MeOH:H2O (2:1) and stirred for 30 minutes at room temperature. After consumption of starting material (TLC analysis), the reaction was filtered through celite and washed with Et2O (30 mL). The organic layer was extracted with 1 M NaOH(aq) (3 × 30 mL) and the organic and aqueous layers collected separately. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 3. The aqueous layer was acidified with 1 M HCl(aq) (100 mL) and extracted with Et2O (2 × 30 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 16. The crude products were purified by preparative TLC (20% acetone:80% pet. spirit) to yield 3 as a yellow solid (5.1 mg, 37%) and 16 as a yellow solid (6.7 mg, 45%). The same procedure with1 yielded 3 (6.1 mg, 43%) and 16 (5.6 mg, 37%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11%; 84% | With iron; acetic acid; In ethanol; water; at 20℃; for 1.0h;Sonication; | A mixture of 2 (0.030 g, 0.058 mmol) and Fe(0) (0.033 g, 0.584 mmol) wasdissolved in 6 mL CH3COOH:EtOH:H2O (1:1:1) and sonicated for 1 hour at room temperature. After consumption of starting material (TLC analysis), the reaction was filtered through celite and washed with EtOH (30 mL). The mixture was concentrated under vacuum and redissolved in Et2O (30 mL). The organic layer was extracted with 1 M NaOH(aq) (3 × 30 mL). The organic and aqueous layers were separated. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 3. The aqueous layer was acidified with 1 M HCl(aq) (100 mL) and extracted with Et2O (2 × 30 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 16. The crude products were purified by preparative TLC (20% acetone:80% pet. spirit) to yield 3 as a yellow solid (11.6mg, 84%) and 16 as a yellow solid (1.6 mg, 11). The same procedure with1yielded 3 (11.4 mg, 80.0 %) and 16 (2.1 mg, 14 %). |
51%; 40% | With iron(III) chloride hexahydrate; zinc; In water; N,N-dimethyl-formamide; at 20℃; for 3.0h; | A mixture of 2 (0.030 g, 0.058 mmol), FeCl3.6H2O (0.076 g, 0.281 mmol) and Zn(0) dust (0.078 g, 1.198 mmol) was dissolved in 3 mL DMF:H2O (1:1) and stirred for 3 hours at room temperature. After consumption of starting material (TLC analysis), the reaction was filtered through celite and washed with Et2O (30 mL). The organic layer was extracted with 1 M NaOH(aq) (3 × 30 mL) and the organic and aqueous layers collected separately. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 3. The aqueous layer was acidified with 1 M HCl(aq) (100 mL) and extracted with Et2O (2 × 30 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give crude 16. The crude products were purified by preparative TLC (20% acetone:80% pet. spirit) to yield 3 as a yellow solid (5.9 mg, 40%) and 16 as a yellow solid (7.1 mg, 51%). The same procedure with1 yielded 3 (7.6 mg, 53%) and 16 (4.8 mg, 32% yield). |
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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