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CAS No. : | 86-79-3 | MDL No. : | MFCD00004962 |
Formula : | C12H9NO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GWPGDZPXOZATKL-UHFFFAOYSA-N |
M.W : | 183.21 | Pubchem ID : | 93551 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 hydroxide; In water; at 110℃; for 4.75h; | Example 1 l-(2-Methoxy-9H-carbazol-9-yl)-3,3-dimethylbutan-2-oneStep A. 2-Methoxy-9H-carbazole2-?ydroxycarbazole (4.83 g) was suspended in 100 mL water. A solution of 1.11 g NaOH in 100 mL water and 3.83 g dimethyl sulfate were added. The mixture was heated in 110 C oil bath for 2.5 hours. After cooling the reaction mixture was filtered. The collected solid was washed with 100 mL each of water and 0.25 M NaOH solution to give a solid. The filtrate and wash was extracted with 4x50 mL ether. This ether solution was combined with 250 mL ethyl acetate solution of the solid collected and washed with 0.2 N NaOH, water, and saturated brine to give a mixture of product and the starting material. This crude product was treated with 6 mL 5 N NaOH and 4.0 mL dimethyl sulfate in 300 mL water at 110 C for 45 minutes. Then, 12.0 mL 5 N NaOH was added and the resulting mixture stirred for 30 minutes. An additional 2.0 mL dimethyl sulfate was added and the resulting mixture heated for another hour. Repeat this sequence with 4.0 mL 5 N NaOH and 2.0 mL dimethyl sulfate. After cooling the reaction mixture, it was filtered to collect the solid product. It was washed with water and dried to give the crude product. It was purified on SGC using 30-55% EtOAc in hexanes to give the title compound as a yellow solid. 1HNMR (CD3OD, 500 MHz) ? 7.92 (d, 7.8 Hz, IH), 7.89 (d, 8.5 Hz, IH), 7.37 (d, 8.0 Hz, IH), 7.25-7.28 (m, IH), 7.08-7.11 (m, IH), 6.96 (d, 2.3 Hz, IH), 6.77 (dd, 2.3 & 8.7 Hz, IH), 3.87 (s, 3H). LC-MS: 3.31 min. (m/Z = 198.1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Synthesis of 2-methoxy-9H-carbazole: MeI (1.25 mL, 20 mmol, 1.0 eq) was added to a mixture of 9H-carbazol-2-ol (3.66 g, 20 mmol, 1.0 eq) and K2CO3 (2.76 g, 20 mmol, 1.0 eq) in DMF (40 mL). The mixture was stirred at room temperature for 23 hours, then quenched by water. The precipitate was filtered off and washed with ethyl acetate, and the collected solid was dried in air to afford the desired product as a white solid 1.94 g in 49% yield. 1H NMR (CDCl3, 500 MHz): delta 3.91 (s, 3H), 6.86 (dd, J=8.0, 2.5 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.93-7.98 (m, 3H). |