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CAS No. : | 23432-43-1 | MDL No. : | MFCD00024011 |
Formula : | C9H6ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XXGUQCVVGPZTPF-UHFFFAOYSA-N |
M.W : | 179.60 | Pubchem ID : | 220929 |
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: |
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* 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 |
---|---|---|
88% | Add 6-chloro-4-oxo-2,3-dihydroquinoline (0.01 mol) to a 25 ml reaction flask, add 15 ml of acetonitrile, acetic acid (0.01 mol), stir for 20 minutes, and slowly add hydrogen peroxide (0.03). Mol), the reaction was stirred at 65 C, the progress of the reaction was monitored by TLC, and the reaction was stopped after 7 hours. After the reaction liquid is cooled to room temperature, it is poured into 50 ml of water, stirred and filtered to obtain a crude product of 5-dichloro-4-hydroxyquinoline, which is separated by silica gel column chromatography (column chromatography silica gel 100-200 mesh, eluent) Petroleum ether: ethyl acetate = 1:4), and the eluent was concentrated to give the product. The yield was 88%, and the purity was 96%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diphenylether; at 220℃; for 0.666667h; | General procedure: A solution of compound 2 in phenoxybenzene was prepared. The mixture was stirred for 40 min at 220 C. The mixture was cooled to room temperature and hexane was added. The solids were collected by filtration and washed with hexane to provide the target compound. The compound was used without further purification. 4-hydroxyquinoline-6-carbonitrile (3a) 3a was prepared by the methods described above from 5-(((4-R-phenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (2), where R is carbonitrile, to prepare a white solid (yield 65%). ESI-MS m/z: 171 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In diphenylether; at 240℃; for 0.5h;Heating / reflux; | A mixture of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid, 21.62 g, 0.15 mol) and trimethyl orthoformate (150 mL) was heated to a gentle reflux under nitrogen for 1 hour. The resulting red solution was cooled (80 C.) and 4-chloroaniline (19.14 g, 0.15 mol) was added portionwise resulting in the formation of a yellow solid. The reaction mixture was heated to reflux, stirred vigorously for an additional hour, and then cooled to 25 C. (see Ryan et al. (2006) Org. Lett. 8:2779-2782; Madrid et al. (2005) Bioorg. Med. Chem. Lett. 15:1015-1018). The resulting solid was filtered and washed with cold acetone to afford the ene-amine compound (29.58 g, 70%, mp. 214-214.5 C. (dec.)) as yellow solid which was characterized by 1H NMR. To a solution diphenyl ether (20 mL) at 240 C. was added the ene-amine compound (5 g, 17.75 mmol) in small portions resulting in vigorous gas evolution and the reaction was bought to reflux for 30 minutes under nitrogen. The reaction mixture was allowed to cool to 80 C. and the precipitate was isolated by filtration and washing with acetone and hexane until the filtrate was colorless. The brown solid was purified by digestion with ether followed by distillation under reduced pressure to give 6-chloroquinolin-4-ol as light-yellow solid in 55% yield (1.7533 g, m.p. 281-282.5 C. (see Riegel et al., (1946) J. Am. Chem. Soc. 68:1264-1266, m.p. 274-275 C.). 1H NMR (400 MHz, CDCl3): 6.07 (1H, d, J=7.4 Hz), 7.59 (1H, d, J=8.8 Hz), 7.68 (1H, dd, J=8.8, 2.5 Hz), 7.95 (1H, d, J=7.4 Hz), 8.01 (1H, d, J=2.4 Hz), 11.92 (1H, bs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(b) 6-Chloro-4-hydroxyquinoline From 6-chloro-4-hydroxyquinoline-3-carboxylic acid ethyl ester, reacted in a manner similar to that described in Example 12, there was obtained the above-named compound of mp 265-268 after recrystallization from ethanol. |