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CAS No. : | 1670-84-4 | MDL No. : | MFCD00231036 |
Formula : | C9H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFHUJFBEFDVZPJ-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 594832 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
90% | In P,P-dichlorophenylphosphine oxide; | b 2-Cyanoindole A solution of indole-2-carboxamide (3.02 g, 18.8 mmol) in dichlorophenylphosphine oxide (20 mL) was heated at 80 C. overnight. The cooled reaction mixture was then poured over 100 mL ice and the pH was adjusted to 11 with 50% aqueous sodium hydroxide. Extraction with ethyl acetate followed by concentration in vacuo gave an off-white solid which was purified by silica gel chromatography (1% MeOH/CH2 Cl2) to yield the title compound (2.41 g, 90%): 1 H NMR (400 MHz, DMSO-d6) delta 7.68 (d, 1H), 7.46 (d, 1H), 7.36 (s, 1H), 7.34 (t, 1H), 7.14 (t, 1H). |
66.4% | With trichlorophosphate; In chloroform; for 2h;Heating / reflux; | Ib) lH-Indole-2-carbonitrile; A mixture of 8.96 g (56 mmol) of lH-indole-2-carboxylic acid amide, 26.0 ml (279 mmol) of phosphorus oxychloride and 230 ml of chloroform is refluxed for 2h. The reaction mixture is cooled to 20 C, poured into 100 ml of water and stirred for Ih. After separation the organic layer is dried over sodium sulfate and concentrated. The residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and hexane-ethyl acetate = 4: 1 as eluent to yield 5.28 g (66.4 %) of the title compound. Mp.: 94-95 C. |
To a cooled solution of indole-2-carboxylic acid(2.0 g, 12.4 mmol) in 60 mL of anhydrous Et20 was added 1.9 mL of SOCl2 (26 mmol). After stirring for 40 min at RT, the ether was removed under reduced pressure at a temperature not exceeding 35 C. The obtained acyl chloride was dissolved in 40 mL of anhydrous Et20 and the resulting solution was added immediately to a stirred solution of liquid ammonia in 80 ml of Et20. The reaction mixture was stirred at RT for 24 h. The solvent was then evaporated under reduced pressure, and the white indole-2-carboxamide was crystallized from 50% aq EtOH and dried in air, after which it was dissolved in POCI3 and heated under reflux for 5 min. The cooled solution was poured onto crushed ice and aq NH4OH was added to maintain a basic pH. The aqueous mixture was extracted with Et20, the extracts were dried over Na2S04 and evaporated. The brown indole-2-carbonitrile 60a (63.3% overall yield from indole-2-carboxylic acid) was obtained. 1H NMR (500 MHz, CDC13) delta 8.56 (br, s, 1 H), 7.68 (d, 1 H, J = 8.0 Hz), 7.43-7.34 (m, 2 H), 7.24-7.21 (m, 2 H). MS (ESI) m/z 144.0 (M + H)+, 140.8 (M -H)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 60℃; for 3h; | To a solution of the crude amide obtained in the above step (1) inTHF (30 ml), BMS (1.18 ml, 12.42 mmol) was slowly added at 0 °C. Theresulting reaction mixture was heated to 60 °C for 3hrs, quenched with 5percent HCIat 0 °C, extracted with EA, and washed with 5percent HCI. The aqueous layerswere combined and basified with 1N NaOH, and again extracted with EA.The organic layers were combined and concentrated to obtain the titlecompound (0.28 g) as yellow oil.TLC System 1 : MC/MeOH =90:10 v/v Rf=0.151H-NMR (300MHz, CDCI3) 8 ppm: 3.98(s, 2H), 7.08(m, 3H),7.26(m, 1H), 7.58(d, 1H), 9.10(brs, |
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