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CAS No. : | 903557-01-7 | MDL No. : | MFCD13179386 |
Formula : | C10H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LGEXBNZXXJFYEB-UHFFFAOYSA-N |
M.W : | 172.18 | Pubchem ID : | 58686845 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With N,N,N,N,-tetramethylethylenediamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 180℃; for 0.08333330000000001h;Microwave irradiation; | Step 1-3: To a DMF solution (14.5 mL) of the compound (3.00 g) obtained in Step 1-2, zinc cyanide (1.04 g) , Pd2(dba)3 (122 mg) , Xantphos (154 mg) and TMEDA (590 muL) were added and the mixture was stirred under microwave irradiation (1800C) for 5 minutes. To the reaction mixture, CHCl3 was added and the mixture was filtrated by Celite and washed with DMF. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane = 50/50 to 100/0; v/v) . To the solid substance obtained, EtOAc was added at room temperature and the mixture was stirred for 30 minutes. A solid substance was obtained by filtration and washed with EtOAc to obtain 2-oxo-l, 2, 3,4- tetrahydroquinoline-7-carbonitrile (15.5 g, a light yellow solid) .1H NMR (600 MHz, CDCl3, delta) : 2.64-2.68 (m, 2H), 3.00-3.04 (m, 2H), 7.04 (s, IH), 7.23-7.29 (m, 2H), 8.46 (brs, IH); ESl/APCI MS m/z 173 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nickel; formic acid / water monomer / 2 h / 100 °C 2: sodium tetrahydridoborate / methanol / 3 h / 0 - 15 °C |