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CAS No. : | 19501-58-7 | MDL No. : | MFCD00012945 |
Formula : | C7H11ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FQHCPFMTXFJZJS-UHFFFAOYSA-N |
M.W : | 174.63 | Pubchem ID : | 2723904 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-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 |
---|---|---|
58% | With sulfuric acid In N,N-dimethyl acetamide at 55℃; for 2 h; | 3-(2-Hydroxyethyl)-5-methoxy-lH-indole (5-methyoxytryptophol) (11): No special precaution was taken to excludeambient oxygen from the followingreaction. 4-methoxyphenylhydrazine hydrochloride (1.214 g, 6.95 mmol) was dissolved in a mixture of I 0 mL 0.72 M H2S04 and J 0 mL DMA, and heated to 55 °C. Next, 2,3- d ihydrofuran (0.525 rnL, 6.95 mmol) was added slowly over 2 minutes. The reactionmixture was sti1red at to 55 oc for 2 h after which time it was cooled to ambienttemperature and ex tracted with isopropylacetate (2 x 25 mL). The combined organiclayers were washed with H20 (3 x 20 mL) and saturated NaCl (1 x 20 mL), dried with Na2S04, filtered and concentrated. The crude residue was purified via flashcolwnnchromatography (50:50 ethyl acetate/hexanes) to afford 11 as an orange-red oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: With hydrogenchloride; sodium nitrite In water for 1.75 h; Cooling Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.5 h; |
To asolution of p-anisidine (4.93 g, 40mmol) in water (12 mL) and conc. HCl (12 mL) was added a solution of sodiumnitrite (3.3 g, 46.40 mmol) in water (10 mL) dropwise at -5 oC overthe period of 15 min. The reaction mixture was stirred for 1.5 h and a solutionof SnCl2 (16.00 g, 84.40 mmol) in conc. HCl (25 mL) was addeddropwise and stirred manually in spite of bulky precipitation. After thereaction mixture was stirred at 0 oC for 30 min, the precipitate wascollected by filtration, washed with water (20 mL), ethanol (12 mL), and Et2O(50 mL) and dried in vacuo to give compound 4 (5.40 g, 31.00 mmol, 77percent) as a pink solid: Rf =0.23 (n-hexane : EtOAc = 2:1); 1H NMR (400MHz, D2O) δ6.94 (2H, d, J = 8.8 Hz), 6.84 (2H, d, J = 8.8Hz), 3.64 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 70℃; for 4.5 h; | (Intermediate Example 38) 5-Methoxy-1-methyl-1H-indole-3-carboxylic acid 4-Methoxyphenylhydrazine hydrochloride (200 mg) and methyl 3,3-dimethoxypropionate (194 mg) were added to acetic acid (8.0 ml) and stirred for 4.5 hours at 70°C. The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (eluding solvent; ethyl acetate: n-hexane 1: 5 --> 1: 3) to give methyl 5-methoxy-1H-indole-3-carboxylate (259 mg, Y.: 97percent). 1H NMR; (DMSO-d6) δ (ppm): 3.8 (3H, s), 3.9 (3H, s), 6.8 (1H, dd), 7.4 (1H, d), 7.5 (1H, d), 8.0 (1H, s), 11.8 (1H, brs). ESI/MS (m/z): 204 (M-H)-. |
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