* 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.
Reference：
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 239 - 244
2
[ 40516-46-9 ]
[ 62-53-3 ]
[ 26892-90-0 ]
Yield
Reaction Conditions
Operation in experiment
86%
for 3.5 h; Reflux
Weigh aniline (1.0 mL) and diethyl ethoxymethanemalonate (2.2 mL), add to the appropriate amount of ethanol, heat to reflux for three hours, cool to room temperature, add 40 mL of phenyl ether, and reflux under heating for 30 min.After cooling to room temperature, after completion of the reaction, ice water was added and extracted with ethyl acetate (100 mL×2).The combined organic phase was washed with brine, dried over anhydrous sodium sulfateThe residue was subjected to silica gel column chromatography to give the product(86percent yield).
Reference：
[1] Patent: CN108623589, 2018, A, . Location in patent: Paragraph 0141; 0148
3
[ 40516-46-9 ]
[ 13720-94-0 ]
Reference：
[1] Patent: CN108623589, 2018, A,
[2] Patent: CN108623590, 2018, A,
4
[ 40516-46-9 ]
[ 615-36-1 ]
[ 35975-57-6 ]
Reference：
[1] Patent: CN108623590, 2018, A, . Location in patent: Paragraph 0148
5
[ 40516-46-9 ]
[ 206258-97-1 ]
Reference：
[1] Patent: CN108623590, 2018, A,
6
[ 40516-46-9 ]
[ 337909-10-1 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 239 - 244
7
[ 40516-46-9 ]
[ 1379615-56-1 ]
Reference：
[1] Patent: CN108623589, 2018, A,
[2] Patent: CN108623590, 2018, A,
Weigh aniline (1.0 mL) and diethyl ethoxymethanemalonate (2.2 mL), add to the appropriate amount of ethanol, heat to reflux for three hours, cool to room temperature, add 40 mL of phenyl ether, and reflux under heating for 30 min.After cooling to room temperature, after completion of the reaction, ice water was added and extracted with ethyl acetate (100 mL×2).The combined organic phase was washed with brine, dried over anhydrous sodium sulfateThe residue was subjected to silica gel column chromatography to give the product(86% yield).
Stage #1: diethyl (ethoxymethylene)malonate; 3-chloro-aniline In ethanol for 3h; Reflux;
Stage #2: for 0.5h; Reflux;
1.1 Step 1) Ethyl 7-chloro-4-hydroxyquinoline-3-carboxylate
Weighing m-chloroaniline (1.0 mL) and diethyl ethoxymethanemalonate (2.2 mL) into an appropriate amount of ethanol.Heat to reflux for three hours, cool to room temperature, add 40 mL of phenetole, and reflux under heating for 30 min.After cooling to room temperature, after completion of the reaction, ice water was added, and ethyl acetate was extracted (100 mL×2), and the organic phase was combined.The organic phase was washed with brine, dried over anhydrous sodium sulfateThe residue was purified by silica gel column chromatography.
Weigh o-bromoaniline (1.0 mL) and diethyl ethoxymethanemalonate (2.2 mL) into an appropriate amount of ethanol.Heat to reflux for three hours, cool to room temperature, add 40 mL of phenetole, and reflux under heating for 30 min.After cooling to room temperature, after completion of the reaction, ice water was added, and ethyl acetate was extracted (100 mL×2), and the organic phase was combined.The organic phase was washed with brine, dried over anhydrous sodium sulfateThe residue was purified by silica gel column chromatography.
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