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With potassium hydroxide; In water; dimethyl sulfoxide; at 70℃; for 21h;Inert atmosphere;
Example 4 4-(4-amino-3-chlorophenoxy)-7-methoxyquinoline-6-carboxamide?monohydrate (0153) (0154) A mixture of 4-amino-3-chlorophenol hydrochloride (593.4 g), a 48.7 w/w % potassium hydroxide aqueous solution (730.6 g), <strong>[417721-36-9]4-chloro-7-methoxy-quinoline-6-carboxamide</strong> (600.0 g), and dimethylsulfoxide (5.4 L) was stirred under nitrogen atmosphere at 70 C. for 21 hours. After 3.0 g of seed crystals was introduced into the reaction solution, hydrous acetone ( acetone: 3 L, purified water: 6 L) was added at 55 C. and cooled to 8 C., and the precipitated deposit was filtered. The deposit was washed with hydrous acetone, and the solid obtained using a rotary evaporator was dried at 60 C. under reduced pressure to thereby obtain 4-(4-amino-3-chlorophenoxy)-7-methoxy-quinoline-6-carboxamide?monohydrate (862.7 g, yield: 94%).
94.44%
Potassium hydroxide (41.50 g, 3.5 eq) was added to a three-neck reaction flask containing 500 ml of dimethyl sulfoxide containing 10% water.SM2 (57.00 g, 1.5 eq) was added in one portion at room temperature. After the addition is completed, the mixture is stirred at room temperature for about 3 minutes.50.00 g of the compound of formula 1 was added in one portion, the temperature was raised to 110 C, and the reaction was kept for 2 h.Acetone was added while hot: water = 1:10 (1.5 L), and the mixture was decanted to room temperature, and the filter cake was collected by filtration, and dried under vacuum at 45 C overnight.Collecting 68g of reddish brown solid formula 2 compound,The purity of the reaction solution was 97.81%.The crude product had a purity of 98.51% and a yield of 94.44%.
64.01%
With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; water; at 2 - 85℃; for 8h;
9.89 g of 4-amino-3-chlorophenol hydrochloride and 100 mL of 1-methylpyrrolidone were taken in a flask and cooled to 2-8oC. 8.3 g of potassium hydroxide dissolved in 10 mL of water was added to the above flask. 10.Og of <strong>[417721-36-9]4-chloro-7-methoxyquinoline-6-carboxamide</strong> was added to the above flask and the contents were heated to 80-85oC and maintained for 8 hours. 400 mL of 10% 1-propanol solution was added to the above flask and stirred. The contents were filtered and washed with 50 mL of 10% 1-propanol solution. The filtered compound was dried under reduced pressure at 56oC to obtain the title compound. The title compound was taken in a flask along with 88 mL of dimethylacetamide and heated to 60-65oC. The seed compound 4-(4-amino-3-chlorophenoxy)-7-methoxyquinoline-6-carboxamide was added followed by addition of 88 mL of 1-propanol. The contents were cooled to 25-3OoC and maintained for 3-4 hours. The contents were filtered and washed with 20 mL of 1-propanol. The filtered compound was dried under reduced pressure 76oC to obtain 4-(4-amino-3 -chlorophenoxy)-7-methoxyquinoline-6-carboxamide.Yield: 64.0 1%; HPLC purity: 99.8%
101 g
With potassium hydroxide; In water; dimethyl sulfoxide; at 25 - 80℃; for 8h;
<strong>[417721-36-9]4-chloro-7-methoxyquinoline-6-carboxamide</strong> compound of formula-7 (100 g) was added the mixture of 4-amino-3-chloro-phenol hydrochloride (102.7 g), aqueous potassium hydroxide solution (71.13 g of potassium hydroxide in 75 ml of water) and dimethyl sulfoxide (900 ml) at 25-30C. Heated the reaction mixture to 75-80C and stirred for 8 hours at the same temperature. The reaction mixture was cooled to 50-55C, aqueous acetone was added to reaction mixture and stirred for 10 minutes. The reaction mixture was cooled to 0-5C and stirred for 1 hour at same temperature. Filter the precipitated solid, washed with aqueous acetone and dried. N-Methyl-2-pyrrolidone was added to the above obtained solid at 25-30C. Heated the mixture to 75-80C and stirred for 15 minutes at the same temperature. The mixture was cooled to 50-55C, ethyl acetate was added to the mixture and stirred for 5 minutes. Cool the mixture to 25-30C and stirred for 2 hours at same temperature. Filtered the precipitated solid and washed with ethyl acetate. The obtained solid was slurried in acetone, filtered and washed with acetone, dried to get the title compound. Yield: 101 g, Purity by HPLC: 99.96%, MR: 2l5-225C.
4-((2-chloro-4-hydroxyphenyl)amino)-7-methoxyquinoline-6-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
13.5 g
With potassium iodide; In ethanol; for 20h;Reflux;
4-Chloro-7-methoxyquinolin-6-amide (10g) and4-amino-3-chlorophenol hydrochloride (11.5 g),Potassium iodide (25 g) was added to the reaction flask, and ethanol (150 ml) was added thereto, and the mixture was stirred and heated to reflux.Stir the reaction for 20 hours,The reaction was monitored by TLC (developing solvent: dichloromethane: methanol = 10:1,4-((2-chloro-4-hydroxyphenyl)amino)-7-methoxyquinoline-6-carboxamide, Rf value 0.3),The reaction solution was cooled to room temperature, and water (450 ml) was added to stir and crystallize for 2 hours.filterThe target product was 13.5 g (mass yield 135percent),The HPLC purity was 98.7percent.
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